Journal of the American Chemical Society p. 1658 - 1665 (1982)
Update date:2022-07-29
Topics: Reactions Hydrolysis Experimental
Ross, Angela M.
Pohl, Terese M.
Piazza, Kathryn
Thomas, Michael
Fox, Bonnie
Whalen, Dale L.
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) showed kinetic terms in HO- at pH > ca. 13.Specific chloride effects attributed to nucleophilic addition of Cl- to neutral epoxide were observed for those compounds (3, 4, and 8) hydrolyzed in KCl solutions.From kinetic and product studies, mechanisms for hydrolyses of the vinyl epoxides are postulated.Acid-catalyzed hydrolyses of 3, 4, 5, and 6 were found to be A-1 in nature, proceeding via intermediate allyl cations.Product distributions depended on the structure of the cation.Mechanisms and product distributions for the spontaneous hydrolyses of vinyl epoxides were found to be variable, and dependent on the structure of the epoxide.
View MoreShandong Hongxiang Zinc Co., Ltd
Contact:086-0311-66187879
Address:DaWang developing zone
Zhengzhou Xinlian Chemical Tech Co. ,Ltd
Contact:0371-65771781 021-52042910
Address:H Part, Building I, No. 700 Gonglu Road, Pudong New Area, Shanghai
Contact:--
Address:80G, No.1 Building, Guodu Development Mansion, No. 182 Zhaohui Road, Hangzhou City, Zhejiang Province,China.
Contact:--
Address:80G, No.1 Building, Guodu Development Mansion, No. 182 Zhaohui Road, Hangzhou City, Zhejiang Province,China.
Contact:(1) 206-3550089
Address:5115 NE 8TH PL, Renton, WA 98059 USA
Doi:10.1016/S0022-328X(01)01013-0
(2001)Doi:10.1016/S0040-4039(01)84866-8
(1972)Doi:10.1063/1.454387
(1988)Doi:10.1515/znb-2001-0907
(2001)Doi:10.1021/ja00768a057
(1972)Doi:10.1016/0040-4039(80)80011-6
(1980)