Vinyl epoxide hydrolysis reactions

…, K Piazza, M Thomas, B Fox, DL Whalen

Index: Ross, Angela M.; Pohl, Terese M.; Piazza, Kathryn; Thomas, Michael; Fox, Bonnie; Whalen, Dale L. Journal of the American Chemical Society, 1982 , vol. 104, # 6 p. 1658 - 1665

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Citation Number: 48

Abstract

Abstract: The rates of hydrolysis of cyclopentadiene oxide (3), cyclohexadiene oxide (4), cycloheptadiene oxide (5), cyclooctadiene oxide (6), butadiene oxide (7), and styrene oxide (8) have been determined as a function of pH. Each epoxide exhibited acid-catalyzed hydrolysis at low pH, and 3-5 showed significant rates for" spontaneous" reaction with solvent at intermediate pH values. The hydrolyses of several of the vinyl epoxides (4 and 5 ...