Dimethylboron bromide and diphenylboron bromide: cleavage of acetals and ketals

Y Guindon, C Yoakim, HE Morton

Index: Guindon, Yvan; Yoakim, Christiane; Morton, Howard E. Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 3912 - 3920

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Citation Number: 161

Abstract

The cleavage of various acetal and ketal derivatives by the use of dialkyl-and diarylboron halides is described. Acetals and ketals readily react with dimethylboron bromide or diphenylboron bromide at-78" C to give the corresponding carbonyl compounds in excellent yield. Under similar reaction conditions MEM, MOM, and MTM ethers are smoothly converted to alcohols. Acetonides are also cleaved with dimethylboron bromide while ...

~52%

~40%

~0%

~0%

~5%

~80%

~0%

~78%

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