The Journal of Organic Chemistry

Direct introduction of the diazo function in organic synthesis

JB Hendrickson, WA Wolf

Index: Hendrickson,J.B.; Wolf,W.A. Journal of Organic Chemistry, 1968 , vol. 33, # 9 p. 3610 - 3618

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Citation Number: 125

Abstract

For synthetic purposes, introduction of the diazo function at methylene positions flanked by two carbonyl groups proceeds smoothly with tosyl azide-sodium hydride or. p- carboxybenzenesulfonyl azide-triethylamine and leads to no separation problems after reaction. With methine positions the same introduction of diazo occurs with cleavage of one acyl residue as with an N-sulfonylamide. Hydrolysis of diazo diketones with alkali is ...

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