Journal of the Chemical Society. Perkin transactions II p. 373 - 382 (1984)
Update date:2022-09-26
Topics:
Waring, Anthony J.
The well known rearrangements of α-santonin (2) to α-desmotroposantonin (3) in aqueous sulphuric acid, and to its acetate in acetic anhydride, have been reinvestigated.No evidence was found for the formation of isomeric products apart from the known β-desmotroposantonin (4).Kinetic and basicity measurements, allied to the use of acidity functions, allow the conclusion that, in >45percent H2SO4, α-santonin (2) rearranges slowly to trans-desmotroposantonin, which rapidly epimerises to (3).In more dilute acid there is evidence of a change in mechanism.The cation of 6-epi-α-santonin (5) rearranges about 1 000 times faster than those of α-santonin and a number of analogues, including the lactone-free analogue (6).This is attributed to a favourable interaction between the lactone ring of (5) and the dienone ring over which it can be closely folded.
View MoreXi'an caijing Opto-Electrical Science & Technology Co., LTD
Contact:+86-29-88294447
Address:NO.168 Zhangba Rd. East, Xi'an, P.R.China
Wuxi Morality Chemical Co., Ltd(expird)
Contact:
Address:B/7F, 321th WuYun Rd, Wanda Plaza, Wuxi City, 214174, China
Fujian Wanke Pharmaceutical Co., LTD.
Contact:+86-598-5026002
Address:Economic development zone,jiangle county
website:http://www.sjc.com.tw
Contact:(886) 2-2396-6223
Address:14Fl., No. 99. Sec. 2, Jen Ai Road
Hubei ShiNan Pharmaceutical Chemical co., Ltd.(expird)
Contact:+86-13554447107
Address:Wuhan HongShanOu wu no road 378 future residence building 1 unit 14 layer no. 1401 A
Doi:10.1021/ja511622e
(2015)Doi:10.1039/c2ob25327e
(2012)Doi:10.1016/0022-328X(91)80160-L
(1991)Doi:10.1248/cpb.26.472
(1978)Doi:10.1016/0022-328X(91)80178-M
(1991)Doi:10.1007/BF00961259
(1991)
