Neighboring Group Participation of Thiofenchone with Acyl Chlorides: Novel Formation of 2-Acyloxy-2,7,7-trimethylnorbornan-1-thiols

Reaction of thiofenchone with acyl chlorides in the presence of AlCl3 in refluxing dichloromethane gave Wagner–Meerwein products and 2-acyloxynorbornan-1-thiols. When ZnCl2 was used as a Lewis acid, norbornan-1-thiols were obtained as major products along with Wagner–Meerwein products. The reaction...

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Bibliographic Details
Published in:Chemistry letters 2017-01, Vol.46 (7), p.960
Main Authors: Okuma, Kentaro, Yamaguchi, Hazuki, Nagatoshi, Risa, Matsui, Hiroyuki, Iwashita, Hidefumi, Nagahora, Noriyoshi, Shioji, Kosei
Format: Article
Language:eng ; fre ; ger ; jpn
Subjects:
Aluminum chloride
Dichloromethane
Lewis acid
Refluxing
Thiols
Zinc chloride
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Summary:Reaction of thiofenchone with acyl chlorides in the presence of AlCl3 in refluxing dichloromethane gave Wagner–Meerwein products and 2-acyloxynorbornan-1-thiols. When ZnCl2 was used as a Lewis acid, norbornan-1-thiols were obtained as major products along with Wagner–Meerwein products. The reaction might proceed through 5-membered cyclic carbocation (oxathiacarbocation) intermediates.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.170245