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.
Jinan Trio PharmaTech Co., Ltd
Contact:86-531-88811783；+(0)13153010282
Address:2766 Yingxiu Road, Jinan High-Tech Zone, China
Suzhou Health Chemicals Co., Ltd.
website:http://www.healthchems.com
Contact:13776257979
Address:No. 338, Jingang Avenue,
Fuxin Jintelai Fluorin Chemical Co., Ltd.
Contact:+86-0418-8229599
Address:, 7th Huagong Road, Fluorine industry development zone (Yimatu Town,Fumeng County),Fuxin City, Liaoning Province, China
Shanghai Pinewood Fine Chemical Co., Ltd.
website:http://www.pinewoodchem.com
Contact:0086-21-62417129，62414096
Address:Suite B, 27F, No.2, Lane 600, Tianshan Road, Shanghai
Jiangsu Willing Bio-Tech Co ltd
website:http://www.willingbio.com/
Contact:+86 18796908173
Address:No 18 Guoqiao 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)
