Journal of the American Chemical Society p. 1429 - 1436 (1989)
Update date:2022-08-29
Topics:
Samuel, Steve P.
Niu, Tian-qi
Erickson, Karen L.
The mechanism for the unusual base-induced ring-enlargement reaction of (halomethylene)cyclobutanes to 1-halocyclopentenes was examined by C-13 labeling studies with (bromomethylene)cyclobutane (1), cis- and trans-1-(bromomethylene)-3-ethoxy-2,2-dimethylcyclobutane (15 and 16), and 1-(bromomethylene)-2,2,4,4-tetramethylcyclobutane (22).Two competing processes were found to lead from the vinyl anion to rearranged products: (1) rehybridization of the vinyl anion to a 1,2-carbene-anion, which subsequently undergoes rearrangement, and (2) a Beckmann-like simultaneousmigration of bromide and ring carbon.Both processes subtly bypass the "forbidden" alkyl-to-carbanion shift.
View MoreShijiazhuang Yunxuan Im&Export Co.,Ltd.
Contact:+86-311-83037514
Address:No.6 Hongbin Road
Shanghai Maxchemco Chemical Industry Co., Ltd.
Contact:(86)21-51079223
Address:No.1305-8, B241, the Ecust Park, Huajing Road, Xuhui District, Shanghai
Shanghai Yolne Chemical Co., Ltd(expird)
Contact:+86-21-62960152,61525205,61538832,61538837
Address:Floor 4,building 2, No. 3377, Kangxi Road, Pudong New District, Shanghai, China
Yangling Ciyuan biotech Co., Ltd.
Contact:86-15802970736
Address:2-1804, International Park Mansion, No.2, South Fengdeng Road, Lianhu District
Contact:86-25-51817806
Address:No. 216, middle longpan road, jincheng tower, floor 21-22, nanjing ,china
Doi:10.1002/adsc.201800155
(2018)Doi:10.1021/jp971068c
(1998)Doi:10.1039/b000533i
(2000)Doi:10.1002/hlca.19930760620
(1993)Doi:10.1007/s11164-012-0924-z
(2013)Doi:10.1039/c5cc09518b
(2016)