Methyl deuteration reactions in vinylporphyrins: protoporphyrins IX, III, and XIII

KM Smith, DW Parish, WS Inouye

Index: Smith, Kevin M.; Parish, Daniel W.; Inouye, Warren S. Journal of Organic Chemistry, 1986 , vol. 51, # 5 p. 666 - 671

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Citation Number: 29

Abstract

Base-catalyzed deuteration of the methyl groups in protoporphyrin M dimethyl ester (1) proceeds with differential deuteration; rate of deuteration, as measured by NMR spectroscopy of reaction products, follows the order 3-Me> 1-Me> 5-Me> 8-Me. A simple qualitative theory to explain the differential deuteration is discussed, based on primary (vinyl group on subunit bearing the deuteriated methyl) and secondary (vinyl group on adjacent ...