Helvetica Chimica Acta p. 325 - 343 (1982)
Update date:2022-08-04
Topics:
Hansen, Hans-Juergen
Sliwka, Hans-Richard
Hug, Werner
The (R)-configuration, attributed to (+)-indane-carboxylic acid ((+)-1) by Fredga, is unequivocally confirmed (Scheme 1).Configurational doubts, raised by an erroneous ORD. curve of (-)-1-methylindane ((-)-4) published by Brewster and Buta, are unfounded (cf. the following paper of Brewster and the corrections in <4>).This was further verified by preparing deuteriated 1-methylindanes starting with (-)-(R)-3-phenylbutyric acid ((-)-(R)-5) as well as with (+)-(R)-1 or (-)-(S)-1 (Scheme 2).The ORD. curves of the optically active 4 thus obtained were (disregarding deuterium isotope effects) identical or antipodal, respectively (cf.Fig.1,2, and 7a-e).Optically active methyl indane-1-carboxylates ((-)-(R)-14 or (+)-(S)-<1-2H>-14) show a strong solvent dependence of their ORD. and CD. spectra with a sign inversion occuring in going from isooctane to methanol or benzene.The observed changes can be explained by a change in the population of comformations where the ester carbonyl group is eclipsed either with the C(1),C(2)- or C(1),H-bond, with the n,?*-transition having a slightly different energy and the ester group an essentially enantiomeric environment with respect to its orientation relative to the benzene moiety.
View MoreContact:+86-913-2223392
Address:No. 32, Xinanjing Road, Weinan City, Shaanxi Province, 714000, China
Jiaozuo Zhongwen Trading Coporation Limited
Contact:+86 0391-3553810
Address:East Renmin Road
Anhui Sholon New Material Technology Co., Ltd.
website:http://www.sholonchem.com
Contact:+86-550-5261666
Address:4/F Block B, Beijing Chemical Building.No.520 Tianrun Road ,Science & Education Town Wujin District, Changzhou City Jiangsu Province
Shanghai doly chemical Co.,Ltd
Contact:+86-21-34716221
Address:No.328,WuHe Roard,MinHang,ShangHai China
Weifang Adde Economic And Trade Co.,LTD.
Contact:86-536-8885548
Address:Room 1402,Wanda Plaza B Block,No.958,Yuanfei Road,Kuiwen District
Doi:10.1021/ja01140a039
(1952)Doi:10.1246/bcsj.55.933
(1982)Doi:10.1021/jo00313a001
(1990)Doi:10.1016/S0040-4039(00)86825-2
(1982)Doi:10.1021/om50004a009
(1983)Doi:10.1016/j.tetlet.2017.01.006
(2017)