Journal of the American Chemical Society p. 1157 - 1165 (1992)
Update date:2022-08-05
Topics:
Jefford, Charles W.
Bernardinelli, Gerald
Wang, Ying
Spellmeyer, David C.
Buda, Andrzej
Houk
The conrotatory electrocyclic opening of benzocyclobutene to o-xylylene was studied by means of ab initio molecular orbital calculations. The theory developed earlier to predict the torquoselectivity of ring opening of 3-substituted cyclobutenes was found to be applicable. Experimentally, the ring opening of several 7-substituted benzocyclobutenes, such as the cyano, methoxycarbonyl, and formyl derivatives was examined. o-Xylylenes were obtained in which cyano or ester groups had rotated outwards, whereas the formyl group turned inwards. N,N-Dimethylbenzocyclobutene-7-carboxamide exhibited 75% inward torquoselectivity upon ring opening. A reversal of mode was seen with the 7-methyl derivatives of benzocyclobutene-7-carbonitrile and methyl benzocyclobutene-7-carboxylate in that the 7-methyl substituent manifested overwhelming outward motion.
View MoreDaqing New Century Fine Chemical Co., Ltd.(expird)
Contact:010-57126694
Address:No.39, jinxing cun, honggang district
Anhui Dexinjia Biopharm Co., Ltd
Contact:+86-531-82375818
Address:9 Hexie Road, kaifaqu, Taihe
Shanghai Kefu Chemical Co.,Ltd.
Contact:+86-21-34616196
Address:Room601-602, Xuhui Business Building, No.168, Yude Road, Shanghai
Wuhan Yitongtai Science and Technology Co.,Ltd.
Contact:+86-27-88933550
Address:27th Fl. Bldg. 1, Shuian International Mansion, Heping Ave, Wuhan, Hubei, China
Shanghai Yuantai Chemical Products Co., Ltd
Contact:021--66129803
Address:Chengyin Road,Shanghai,China
Doi:10.1039/c2ob25315a
(2012)Doi:10.1016/j.tetlet.2012.05.041
(2012)Doi:10.1002/ejoc.201402915
(2014)Doi:10.1039/jr9550000631
(1955)Doi:10.1021/jo01145a021
(1951)Doi:10.1055/s-0031-1290527
(2012)