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.
Xinchang Jiu Xin Pharmaceutical Co., Ltd
website:http://www.jiuxinpharm.com
Contact:86 137 5756 8585
Address:Poyang industry Park
Beijing Top Science biological technology co., LTD
Contact:+86-13439059536
Address:15-1705 jre three mile, Beijing 100000,CHINA
Hunan Haili Chemical Industry Co.,Ltd.
Contact:+86-731-85521860
Address:No.251, 2nd Section, Furong Road, Changsha,Hunan,China
WENZHOU M&C FOREIGN TRADE CO.,LTD.
Contact:+86-577-88862917
Address:No.8 Liming West Road,Wenzhou,zhejiang,China
Anhui New Star Pharmaceutical Development Co., Ltd
Contact:013956922763
Address:Floor 3, F9A, F Workshop, No.110 Kexue Road, High-Tech Development Zone, Hefei, Anhui ,China
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)
