Efficient method for the reductive cleavage of acetals and ketals with Zn (BH4) 2/Me3SiCl

H Kotsuki, Y Ushio, N Yoshimura…

Index: Kotsuki, Hiyoshizo; Ushio, Yasuyuki; Yoshimura, Naka; Ochi, Masamitsu Journal of Organic Chemistry, 1987 , vol. 52, # 12 p. 2594 - 2596

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Citation Number: 51

Abstract

As can been seen in Table I, compared to the aromatic acetals the aliphatic ones require a longer reaction time (runs 7 and 8). And the nitro-substituted acetal is reduced extremely slowly (run 4). These results suggest that the reduction presumably proceeds via the resonance-stabilized carbocation intermediate formed by Me3SiC1-promoted cleavage of acetals or ketals. This new method has also been applied for the reductive cleavage of ...

~90%

~41%

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