Tetrahedron p. 1953 - 1960 (1980)
Update date:2022-08-04
Topics:
Doutheau, Alain
Balme, Genevieve
Malacria, Max
Gore, Jaques
Thirteen variously substituted α-ethylenic β'-allenic alcohols (1,5,6-triene-3-ols) have been synthesized by three different methods, for two of which the key step was the reaction of an organo copper reagent with a derivative of a β-hydroxy γ-ethylenic alcohol (1-ene-5-yne-3,7-diol). The[3,3]-sigmatropic rearrangement of these alcohols, following the heating of their solution in diglyme, leads to γ-dienic aldehydes and ketones. The yields are best (60-70%) for tertiary alcohols substituted on carbon 5. Comparisons of the reactivities of these 13 alcohols show that the mechanism of this rearrangement can probably vary, following the substitution from a cyclohexadiyl biradical process to a concerted pathway involving a cyclohexane transition state.
Suzhou Time-chem Technologies Co., Ltd.
Contact:0512-63983931/68086856
Address:No. 1326 of Binhe Road, New District, Suzhou, Jiangsu, P. R. China
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
Yingkou Sanzheng New Technology Chemical Industry Co., Ltd.
Contact:+86-417-2927806
Address:yingkou
JIANGXI ZHANGFENG CHEMICAL CO., LTD.
Contact:+86-0799-3413066
Address:Xiyuan village, Xiabu Town, Xiangdong District
Henan Techway Chemical Co.,Ltd.
website:http://www.techwaychem.com
Contact:+86-371-66380080
Address:No.27 Shunhe Road,
Doi:10.3987/COM-13-12894
(2014)Doi:10.1021/je00024a037
(1981)Doi:10.1016/S0040-4039(00)88143-5
(1983)Doi:10.1002/adsc.201901492
(2020)Doi:10.1016/0040-4039(80)80202-4
(1980)Doi:10.1021/jo00144a007
(1982)
