Diiodosilane. 2. A multipurpose reagent for hydrolysis and reductive iodination of ketals, acetals, ketones, and aldehydes

E Keinan, D Perez, M Sahai…

Index: Keinan, E.; Perez, D.; Sahai, M.; Shvily, R. Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2927 - 2938

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Citation Number: 32

Abstract

The reaction patterns of diiodosilane (SiH212, DIS) with ketals, acetals, ketones, and aldehydes were explored. The reagent may be used for mild cleavage of ketals and acetals either hydrolytically to give the parent carbonyl functionality or reductively to produce the corresponding alkyl iodide. At low temperatures (-42" C) and short reaction times (few minutes), catalytic amounts (5-10 mol%) of DIS provide clean deprotection of various ...

~41%

~94%

~99%

~38%

~97%

~99%

~78%

~98%

~97%

~99%

~96%

~97%

~99%

~85%

~96%

~98%

~97%

~61%

~19%

~48%

~95%

~97%

~11%

~98%

~19%

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