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Sulfur as a Bridge: Synthesis of Medium Rings via a Bicyclic Sulfonium Ion
Author(s) -
Zhou Hongwei,
Xing Yanpeng,
Liu Le,
Hong Junjie
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100502
Subject(s) - sulfonium , chemistry , bicyclic molecule , moiety , sulfur , ring (chemistry) , ion , combinatorial chemistry , organic chemistry , salt (chemistry)
A facile and efficient synthesis of medium rings via a bicyclic sulfonium ion was developed. Spectroscopic evidence for the formation of an intermediate sulfonium moiety is provided. The sulfur atom served as a “bridge” to access the medium ring system and could be removed after use via a Ramberg–Bäcklund process. As a result of the readily available starting materials, simple operation, and mild conditions, these reactions should be an appealing strategy in organic synthesis.