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Silica Gel Triggered Transformations of 3‐Methylenecyclopropylmethyl Sulfonates to 3‐Methylenecyclobutyl Analogues: Experimental and Computational Studies
Author(s) -
Shao LiXiong,
Li YuXue,
Shi Min
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600722
Subject(s) - silica gel , sulfonyl , chemistry , chloride , computational chemistry , chromatography , organic chemistry , alkyl
Methylenecyclopropylcarbinols 1 treated with sulfonyl chloride and Et 3 N form the sulfonated products 3 in almost quantitative yields, which can be transformed to the corresponding 3‐methylenecyclobutyl sulfonates 4 with silica gel chromatography work‐up. The rational explanation was proposed on the basis of computational studies.