Synthetic reactions by complex catalysts. VIII. Copper-catalyzed reactions of thiol and alcohol with diazoacetate

T Saegusa, Y Ito, S Kobayashi, K Hirota…

Index: Saegusa,T. et al. Journal of Organic Chemistry, 1968 , vol. 33, # 2 p. 544 - 547

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Citation Number: 25

Abstract

The reaction of alkylthioacetate (IV) with the carbene from diazoacetate will lead to an S- ylide (A) which by Stevens rearrangement? produces alkylthiosuccinate (V). The proton shift in the S-ylide A, on the other hand, will afford the carbene (C) and diethyl thiodiglycolate (VI) through the intermediate (B). The carbene (C) in turn reacts with diazoacetate to afford the third by-product (VII).

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