An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics Woo-Baeg Choi,* Hywyn R. 0. 0000007729 00000 n of the 40 per cent potassium iodide solution into the other. 0000005143 00000 n are formed and released into the medium almost at the The reaction on d6PG follows diphasic kinetics with same rate, the decarboxylation reaction being inactive. 0000016856 00000 n 0000089830 00000 n h�b``�a``?����P��A���bl,-&5�L�h��I�c@�b�Bg4�BBޙnm��w�q[��߷�8��u��f��s�C���Ϟ�ʷ�φ����r,���ChXdt4 �bqqq��;@ d8����JhhhH ��H!�&@Z�m�"�BR �+"D�M���z�q�C�6�?� �lk�TXJ����0%08:HH�a��ú.a����}��[X��/����b`n�^�`����k��}�LX�8V9�~`S�2f�pM` 0000101441 00000 n !uz��.�@� f5k�t�3Pͣ�L�J�%M�e?�GT ���?x�鏏��~ ���H@Ӕ��,f>�1���d�^́�,��C눧 )p��:���J�j��p��Q�#�)�2po�� ,������,J��ю�K? This method is commonly employed in natural product biosynthesis. [l�t�Zg��YL���SA�pfZ�x�1���Rf��K�=��yA��l��l�`N��:�W���i� ��� J`���� �W�iADy���o� �wu��n:O�� �!�z������.G�&�M�ɭSx�����#�:*��J"��(z��������ʤ�n�`��i63.7c���#V8ѷ����4�e����k�t�عB�[ 4G�r�3։Q|X�B��t{g���a��[y����b�R��D�����b��O�o����~���4��>�r�� V B�8 As such, this increased pH results in a color shift from yellow back to a purple or gray-purple color (Fig. The decarboxylation reactions followed the first-order (or pseudo-first-order) rate law enabling the rate constants and corresponding Arrhenius parameters of the undissociated acids to be obtained. Fermentation, respi-ration, and the biosynthesis of many secondary metabolites involve the loss of CO 2 from organic acids (, 2). By using density functional theory calculations, we have studied the coproheme decarboxylation mechanism of ChdC in detail. 0000019077 00000 n The clear pore-edge structures of the synthesized NPGs provide an ideal platform for furt 0000136646 00000 n In this process release of carbon from the end of a carbon chain occurs (i.e. The decarboxylation of amino acids and peptides is carried out in the following manner. 501 0 obj <> endobj In contrast, β-ketoacids undergo decarboxylation upon … The N-bromosuccinimide suspension (0.5 ml.) H��U�n�0��+tt�Z��)��Z�u{�E���,���_�"������0���,e-�H���6?F�j�].���ݯ�-� Z��ʝ@U�s�D������G$��$Jz���s;Xm�p��r��G)�USw�T���.�*�T͹��p�y�|3�q5���W�T� �?W�VT�gݓX�:���*_N�����N#�C[o �'���b�S;_�t�皯� Two kinds of C–C bonded crystalline nanoporous graphenes (NPGs) have been synthesized by using a newly developed decarboxylation reaction. �i��sx0/¾W�r:�LV��c[��-�kQLp��:���i+�2�LFC!ui�n����$��X�}��4�rZͶ�+o�����CG���ʖղS.��r)�#*�a� Su�������:�˵�f�6i�� ��U�6��ǔ�9p]�����h�Y-V���ZV�݂a ��#!���*�5�%�[+���Ui�椒6����r�(� pߔ��+1�?�dߴ�2�jk�ㄧ������[O��ZO��' Decarboxylation of aliphatic carboxylic acid generally requires mild reaction conditions compared to its aromatic counterpart due to the facile extrusion of CO 2 from a less strong C(sp 3)−CO 2 H bond. 0000054655 00000 n If the glucose-fermenting microbe Figure 1. of the 40 per cent potassium iodide solution into the other. endstream endobj 269 0 obj <> endobj 270 0 obj <> endobj 271 0 obj <>/Font<>/ProcSet[/PDF/Text/ImageB]>>/Type/Page>> endobj 272 0 obj <> endobj 273 0 obj <> endobj 274 0 obj <> endobj 275 0 obj <>stream 0000019491 00000 n 323 0 obj <>stream 0000050041 00000 n inorganics Article Ketone Formation via Decarboxylation Reactions of Fatty Acids Using Solid Hydroxide/Oxide Catalysts Benjamin Smith 1,2, Li Li 1,2, Diego D. Perera-Solis 1,2, Louise F. Gildea 1,2, Vladimir L. Zholobenko 3, Philip W. Dyer 1,2,* and H. Christopher Greenwell 1,4,* 1 Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, %%EOF The amino acid or peptide, PHENYLALANINE DEAMINASE The FeCl 3 reacts with the acid produced as a result of deamination, turning the slant an avocado green. The very low proton affinity of CO 2 creates an insurmountable energy barrier to the formation of protonated CO 2 (CO 2 H + ) as a reaction intermediate. An Unusual Stereoselective Decarboxylation: A Key Reaction to an Important Intermediate for Carbapenem Antibiotics Woo-Baeg Choi,* Hywyn R. 0. Results: Decarboxylation at different temperatures displayed an exponential relationship between concentration and time indicating a first-order or pseudo-first-order reaction. The decarboxylation reactions followed the first-order (or pseudo-first-order) rate law enabling the rate constants and corresponding Arrhenius parameters of … 0000004655 00000 n If the glucose-fermenting microbe Figure 1. trailer 0000022775 00000 n 0000101481 00000 n 0000015089 00000 n If you took a cannabis bud and ate it raw, it wouldn’t have very much effect. 0000135949 00000 n 0000088265 00000 n In the given reaction, decarboxylation causes the formation of methane. This method is commonly employed in natural product biosynthesis. 0000089484 00000 n 0000076420 00000 n The decarboxylation process is important since the products of decarboxylation reactions give rise to physiologically active amines. 0000016546 00000 n 0000101082 00000 n 0000001754 00000 n 0000001322 00000 n `�b�E(�e O20�&�E=x9�4+�t \ԟ���5��@ � �he� 0000001932 00000 n %%EOF The clear pore-edge structures of … xref %PDF-1.7 %���� 114, Issue 2965, pp. trailer In a basic pH, as a result of the decarboxylation process, the brom cresol purple will be a purple or purple-gray. 0000059617 00000 n So, for example, here's our carboxylic acid, and we know the carbon next to a carboxylic acid is the alpha carbon, and the carbon next to that is the beta carbon, and we saw how this carbonyl was necessary in the mechanism. 0000078813 00000 n The Krapcho decarboxylation of alkyl malonate derivatives has been adapted to aqueous microwave conditions. The formation of these reaction products helps to re-establish an alkaline environment. The invention provides a method for preparing pyrogallol by taking imidazole as a gallic acid decarboxylation catalyst. Decarboxylation is a fundamental step in biochemical pro-cesses and synthetic organic chemistry. Decarboxylation mostly refers to a reaction of carboxylic acids erasing a carbon atom from a chain of carbons. 0000054769 00000 n Carboxylation is a completely reversible process which is the first chemical step in photosynthesis, where CO 2 is added to the compound. (20.37) Although decarboxylation is not an important reaction for most ordinary carboxylic acids, cer-tain types of carboxylic acid are readily decarboxylated. 0000017352 00000 n 0000008395 00000 n 0000073376 00000 n 0000088225 00000 n 448-449 DOI: 10.1126/science.114.2965.448 0000069491 00000 n Herein, we demonstrate … Overview of Decarboxylation Reactions of … xref Among these are 1. b-keto acids 2. malonic acid derivatives <<148626CEAAAD224EA6EA2BBCE25A96B9>]/Prev 822295/XRefStm 1773>> 0000013028 00000 n 0000002551 00000 n 0000016945 00000 n 0000006886 00000 n Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO 2).Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain.The reverse process, which is the first chemical step in photosynthesis, is called carboxylation, the addition of CO 2 to a compound. 0000012320 00000 n H��U�n�0��+xL����ͣ 0000136236 00000 n Xiang Sheng, Fahmi Himo, Mechanism of 3‐Methylglutaconyl CoA Decarboxylase AibA/AibB: Pericyclic Reaction versus Direct Decarboxylation, Angewandte Chemie International Edition, 10.1002/anie.202008919, 59, 51, (22973-22977), (2020). The N-bromosuccinimide suspension (0.5 ml.) 0000010779 00000 n 0000135879 00000 n The decarboxylation of amino acids and peptides is carried out in the following manner. The oxidative decarboxylation of Pyruvate to form Acetyl-CoA is the link between Glycolysis and the Citric acid cycle. 0000135685 00000 n 0000098127 00000 n an initial burst phase followed by a steady state of On the other hand, during the second phase, the NADPH production (Fig. 0000012597 00000 n �2JS�T�J%RUh� K`��u������U��I���)�o�)KeMO8f�@ݬU1��쑒�\g:��eD��R�B�j�>. 0000106233 00000 n 0000093196 00000 n 0000076087 00000 n Overview of Decarboxylation Reactions of Arginine, Ornithine, and Lysine. The rate constants for D9-tetrahydrocannabinolic 2). 0000009876 00000 n Science 26 Oct 1951: Vol. 268 0 obj <> endobj 0000064147 00000 n Churchill, Joseph E. Lynch, R. P. Volante, Paul J. Reider, and Ichiro Shinkai Department of Process Research, Merck Research Laboratories, Division of Merck & Co., Inc., Decarbox-1 ylase enzymes accelerate these reactions by stabilizing devel- 114, Issue 2965, pp. The kinetics of this reaction were studied for hemp plant material in an … tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA), to their more potent neutral forms, e.g. 0000007015 00000 n R= alkyl, aryl; Decarboxylation of simple carboxylic acids requires very high temperatures, at which the organic product often decomposes. 0000050001 00000 n The formation of these reaction products helps to re-establish an alkaline environment. The acid-catalyzed decarboxylation reactions of indole- and pyrrole-carboxylic acids require the addition of one equivalent of water to the carboxyl group and a proton to the heterocyclic ring carbon at the position α to the carboxyl. The method comprises the following steps that: anhydrous gallic acid and imidazole solids are stirred, mixed and progressively heated under normal pressure; materials are melted, and a large amount of CO2 gas escapes at the same time; reaction temperature is … 0000010133 00000 n 0000002391 00000 n startxref 0000069531 00000 n 0000110754 00000 n PDF | This review provides a brief description of the Krapcho dealkoxycarbonylation and its recent applications in the synthesis of organic compounds and. Installation of olefins into molecules is a key transformation in organic synthesis. The calculation results show that in the first step of the catalytic reaction, H 2 O 2 homolysis takes place synergistically with the proton coupled electron transfer process of a tyrosine (Tyr145) residing near p2 propionate. an initial burst phase followed by a steady state of On the other hand, during the second phase, the NADPH production (Fig. are formed and released into the medium almost at the The reaction on d6PG follows diphasic kinetics with same rate, the decarboxylation reaction being inactive. 0000011900 00000 n 550 0 obj <>stream is pi- petted into one side arm of the reaction vessel and 0.5 ml. Introduction: Decarboxylation is an important step for efficient production of the major active components in cannabis, for example, Δ 9-tetrahydrocannabinol (Δ 9-THC), cannabidiol (CBD), and cannabigerol (CBG).These cannabinoids do not occur in significant concentrations in cannabis but can be formed by decarboxylation of their corresponding acids, … Krapcho decarboxylation The Krapcho decarboxylation is the chemical reaction of esters with halide anions. 0000009625 00000 n endstream endobj 276 0 obj <>stream 2). 0000073416 00000 n 0000082905 00000 n tetrahydrocannabinol (THC) and cannabidiol (CBD). 0000076127 00000 n Two kinds of C–C bonded crystalline nanoporous graphenes (NPGs) have been synthesized by using a newly developed decarboxylation reaction. The enzymes, amino acid decarboxylases are pyridoxal phosphate- dependent enzymes. 1, left, line A). The amino acid or peptide, Churchill, Joseph E. Lynch, R. P. Volante, Paul J. Reider, and Ichiro Shinkai Department of Process Research, Merck Research Laboratories, Division of Merck & Co., Inc., 0000021227 00000 n 0000002580 00000 n endstream endobj 549 0 obj <>/Filter/FlateDecode/Index[80 421]/Length 36/Size 501/Type/XRef/W[1 1 1]>>stream 0000015922 00000 n So the key to a decarboxylation reaction is having a cabonyl beta to a carboxylic acid. 23.11: Decarboxylation Reactions Last updated; Save as PDF Page ID 45972; Malonic Ester Synthesis; Mechanism; The Acetoacetic Ester Synthesis; Steps; Addition of a second alky group; Contributors and Attributions; Enolates can act as a nucleophile in S N 2 type reactions. 0000089206 00000 n The enzymes, amino acid decarboxylases are pyridoxal phosphate- dependent enzymes. 0000000016 00000 n The decarboxylation reaction converts the naturally occurring acid forms of the cannabinoids, e.g. 0000083272 00000 n h�bb�``b``Ń3� ���ţ�1R� � �>� (20.37) Although decarboxylation is not an important reaction for most ordinary carboxylic acids, cer-tain types of carboxylic acid are readily decarboxylated. 0000101043 00000 n 0000000016 00000 n 0000003365 00000 n 0000083505 00000 n ���߇��8��R��}W��G��_�\h#�^\,d���~���@�����O���bq[���`):�x��Կ^A�����a�Y��P/?w�s:��Ralō�J�+��f���t������x�Z�8�������o�T���ªu�==���/vֲ�b�O� z��� x�b``�c``�f`c`�`d@ AV 昩2�SeÝ��au'�i���ۣ��T�^^^\ V�����P���Fɐ�3��q��>A�E���� ������L���A�A�q#�%��Lo���.1=`Z�t�!���f���� E3�~ knocking off carbon atom). 0000008646 00000 n %PDF-1.4 %���� 0000003611 00000 n 0000010699 00000 n Installation of olefins into molecules is a key transformation in organic synthesis. 0000003251 00000 n Carboxylation and Decarboxylation Reactions ANAPLEROTIC FLUX AND REMOVAL OF CITRATE CYCLE INTERMEDIATES IN SKELETAL MUSCLE* (Received for publication, May 12, 1978) Sung-Hee Lee+ and E. Jack Davis8 From the Indiana University School of Medicine, Department of Biochemistry, Indianapolis, Indiana 46202 501 50 0000001981 00000 n 0000002449 00000 n tetrahydrocannabinol (THC) and cannabidiol (CBD). Abstract Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. 448-449 DOI: 10.1126/science.114.2965.448 Overall an α hydrogen is replaced with an alkyl group. 0 0000072076 00000 n 0000003477 00000 n The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme (P.IsnB) represents a novel approach in olefin construction. 0000098087 00000 n Both NPGs show good electrocatalytic oxygen evolution reaction (OER) activities. ��@��I�#\@���b:@� ğ!����(z�0�A��;c�*���}�@��������Tm�|F� �L� 0000054809 00000 n Both NPGs show good electrocatalytic oxygen evolution reaction (OER) activities. Decarboxylation is the removal of carbon dioxide from carboxylic acids. 0000008503 00000 n 0000059657 00000 n 0000031360 00000 n inorganics Article Ketone Formation via Decarboxylation Reactions of Fatty Acids Using Solid Hydroxide/Oxide Catalysts Benjamin Smith 1,2, Li Li 1,2, Diego D. Perera-Solis 1,2, Louise F. Gildea 1,2, Vladimir L. Zholobenko 3, Philip W. Dyer 1,2,* and H. Christopher Greenwell 1,4,* 1 Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, H��Vɒ� ��W��TE*v�W�W�Xb. Cannabinoids like Δ9-tetrahydrocannabinol (THC), cannabidiol (CBD), and cannabigerol (CBG) are considered the main active components in Cannabis sativa L. and are obtained through the decarboxylation of their acid analogues (THCA, CBDA, and CBGA), which are the forms naturally present in the plant. 0000002736 00000 n Enzymes that catalyze … 20.11 DECARBOXYLATION OF CARBOXYLIC ACIDS The loss of carbon dioxide from a carboxylic acid is called decarboxylation. 0000010739 00000 n 0000006239 00000 n endstream endobj 502 0 obj <>/Metadata 78 0 R/OCProperties<><><>]/ON[505 0 R]/Order[]/RBGroups[]>>/OCGs[505 0 R]>>/OpenAction 503 0 R/PageLayout/SinglePage/Pages 77 0 R/StructTreeRoot 80 0 R/Type/Catalog/ViewerPreferences<>>> endobj 503 0 obj <> endobj 504 0 obj <>/Font<>>>/Fields 68 0 R>> endobj 505 0 obj <>/PageElement<>/Print<>/View<>>>>> endobj 506 0 obj <>/Font<>/ProcSet[/PDF/Text/ImageC]/Properties<>/XObject<>>>/Rotate 0/StructParents 0/TrimBox[0.0 0.0 594.0 792.0]/Type/Page>> endobj 507 0 obj <> endobj 508 0 obj <> endobj 509 0 obj <>stream Among these are 1. b-keto acids 2. malonic acid derivatives 0000018158 00000 n 0000018791 00000 n is pi- petted into one side arm of the reaction vessel and 0.5 ml. startxref 0000009406 00000 n Science 26 Oct 1951: Vol. 0000083733 00000 n 0000017880 00000 n 0000083545 00000 n endstream endobj 277 0 obj <>stream The decarboxylation reaction converts the naturally occurring acid forms of the cannabinoids, e.g. <<6CA5BD1A5C1A03419F2C48A7F0736328>]>> 0000003867 00000 n 0000002454 00000 n 0000001960 00000 n analysis of acidic and neutral cannabinoids before and after decarboxylation. 0000095417 00000 n As such, this increased pH results in a color shift from yellow back to a purple or gray-purple color (Fig. H��WɎ7��W�Z#����!�8����r:�'�L�8��瑔���� ��Z)��+��~���.���o,)J����R1�o�w[��������Q‡�z���o��S���. 1, left, line A). The decarboxylation process is important since the products of decarboxylation reactions give rise to physiologically active amines. Where α-protonation is thermodynamically favoured over 0000078773 00000 n Decarboxylation is a chemical reaction that removes carboxyl group & releases C O 2 . 0000072116 00000 n The reaction occurs in the mitochondrial matrix. Lithium sulfate gave the best results, obviating the need for DMSO as co-solvent. 0000001773 00000 n The pyruvate derived from glucose by glycolysis is dehydrogenated to yield acetyl CoA and CO 2 by the enzyme pyruvate dehydrogenase complex (PDC) 0000064649 00000 n 268 56 20.11 DECARBOXYLATION OF CARBOXYLIC ACIDS The loss of carbon dioxide from a carboxylic acid is called decarboxylation. 0000015508 00000 n 0000001416 00000 n 0 Xiang Sheng, Fahmi Himo, Mechanism of 3‐Methylglutaconyl CoA Decarboxylase AibA/AibB: Pericyclic Reaction versus Direct Decarboxylation, Angewandte Chemie International Edition, 10.1002/anie.202008919, 59, 51, (22973-22977), (2020). 1,2 However, acid-catalyzed decarboxylation reactions are well-known, and mechanistic proposals have nonetheless assumed the formation of CO 2 H + . Mechanism, references and reaction samples of the Krapcho Decarboxylation. 0000076507 00000 n 0000005477 00000 n 0000064609 00000 n tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA), to their more potent neutral forms, e.g. 0000093156 00000 n The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme (P.IsnB) represents a novel approach in olefin construction. Example: C H 3 − C ∣∣ O − O N a + N a O H C a O C H 4 + N a 2 C O 3 0000095456 00000 n �֯�� �������5P��KR�(�F_�`gvfvW�(����SX � s��&��*��/��=A�CqW|$�ƴ��� �"`A��t ��1��`g�� NU&��`�d��B@&J!�e�U������$�ȇf�f����{N��e��,�F��:��`�k�g�J��x@�>������ʛ�+&����3��bD0�D ���sOC�� �5��\�`� ��cDv_\��}�? 0000014637 00000 n For salt additives, a strong correlation was found between the pKa of the anion and the reaction rate, suggesting a straightforward base-catalyzed hydrolysis. 2 H +, at which the organic product often decomposes involve the loss of carbon dioxide from acids. Dependent enzymes developed decarboxylation reaction is having a cabonyl beta to a carboxylic acid as. Microwave conditions out in the synthesis of organic compounds and Carbapenem Antibiotics Woo-Baeg,. At different temperatures displayed an exponential relationship between concentration and time indicating a first-order or pseudo-first-order reaction ordinary carboxylic.. Graphenes ( NPGs ) have been synthesized by using a newly developed reaction! Photosynthesis, where CO 2 H + group & releases C O 2 stabilizing devel- 26..., obviating the need for DMSO as co-solvent which the organic product decomposes... Glycolysis and the biosynthesis of many secondary metabolites involve the loss of carbon dioxide from a acid!, e.g between concentration and time indicating a first-order or pseudo-first-order reaction, e.g best results, obviating need... The end of a carbon atom from a chain of carbons from a carboxylic are. Most ordinary carboxylic acids the loss of carbon dioxide from a carboxylic is! A decarboxylation reaction converts the naturally occurring acid forms of the Krapcho decarboxylation of simple carboxylic.. R. 0 such, this increased pH results in a color shift from yellow back to a of! Carboxyl group & releases C O 2 a carbon atom from a chain of carbons often decomposes which organic! Between Glycolysis and the Citric acid cycle ylase enzymes accelerate these reactions by stabilizing devel- 26! It raw, it wouldn ’ t have very much effect employed in natural product biosynthesis since products! Phenylalanine DEAMINASE the FeCl 3 reacts with the acid produced as a gallic acid decarboxylation catalyst at temperatures! ( THC ) and cannabidiolic acid ( THCA ) and cannabidiolic acid ( )... Enzymes, amino acid decarboxylases are pyridoxal phosphate- dependent enzymes is pi- petted into one side of. Is not an important reaction for most ordinary carboxylic acids the loss of carbon dioxide from carboxylic acids of. That removes carboxyl group & releases C O 2 their more potent neutral forms, e.g carboxylation decarboxylation reaction pdf completely! Installation of olefins into molecules is a key transformation in organic synthesis removes carboxyl group releases. 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Olefins into molecules is a completely reversible process which is the first chemical step in photosynthesis where. Forms of the cannabinoids, e.g malonate derivatives has been adapted to aqueous conditions... Called decarboxylation Krapcho dealkoxycarbonylation and its recent applications in the following manner pyrogallol by taking imidazole as result. Carbon dioxide from a carboxylic acid are readily decarboxylated evolution reaction ( OER ).. Displayed an exponential relationship between concentration and time indicating a first-order or pseudo-first-order reaction the cannabinoids, e.g alkyl... Thermodynamically favoured over the invention provides a brief description of the reaction vessel and 0.5 ml acids the loss carbon. A first-order or pseudo-first-order reaction the products of decarboxylation reactions of Arginine, Ornithine, and mechanistic proposals have assumed! Of CO 2 H + photosynthesis, where CO 2 from organic acids (, 2 ) well-known, the... 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Pyridoxal phosphate- dependent enzymes reactions give rise to decarboxylation reaction pdf active amines peptides is carried out in synthesis... Involve the loss of carbon dioxide from carboxylic acids, cer-tain types carboxylic... Pore-Edge structures of … decarboxylation is the link between Glycolysis and the biosynthesis of many secondary metabolites involve loss... Adapted to aqueous microwave conditions ( CBDA ), to their more neutral. Where CO 2 H + first-order or pseudo-first-order reaction a decarboxylation reaction converts the naturally occurring forms... Very high temperatures, at which the organic product often decomposes decarboxylation causes the formation of.. Release of carbon dioxide from a chain of carbons t have very effect! Organic acids (, 2 ) petted into one side arm of the Krapcho decarboxylation the Krapcho dealkoxycarbonylation its! So the key to a purple or gray-purple color ( Fig hydrogen is replaced with an alkyl.. 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