Journal of the American Chemical Society

the Chemistry of an Electron-Deficient 5-Deazaflavin. 8-Cyano-10-methyl-5-deazaisoalloxazine

RL Chan, TC Bruice

Index: Chan,R.L.; Bruice,T.C. Journal of the American Chemical Society, 1977 , vol. 99, p. 6721 - 6730

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Citation Number: 20

Abstract

Abstract: The syntheses of 8-cyano-3-R-IO-methyl-5-deazaisoalloxazines (111) are described as is a comparison of the reactions of 111 and 3-R-10-methyl-5- deazaisoalloxazine (I) with a number of nucleophiles. Thiol anions, S032-, HS03-, CN-, HO-, and HOz-add to the 5 position of 111. Though RS-species provide no detectable reaction with 1, the pseudo-first-order rate constants for addition to 111 exceed 170 sl. The ...