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Efficient Simmons–Smith cyclopropanation with Zn/Cu and CH 2 I 2
Author(s) -
Fujii Kanami,
Shiine Kodai,
Misaki Tomonori,
Sugimura Takashi
Publication year - 2013
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.2935
Subject(s) - chemistry , solvent , boiling point , cyclopropanation , medicinal chemistry , ether , organic chemistry , catalysis
An appropriate solvent to perform the original Simmons–Smith reaction was reinvestigated. Among available solvents, cyclopentyl methyl ether (CPME), a recently commercialized ethereal solvent, was found to be the best so far. Compared with Et 2 O under reflux – the commonest conditions – reaction completion in CPME at 50 °C was about 10 times faster. The product yields and selectivities were mostly identical to those with Et 2 O, but were better in some cases; e.g. 13–56% with 2‐cyclohexenol. The good performance of CPME should be mainly due to its moderate polarity and high boiling point. Copyright © 2012 John Wiley & Sons, Ltd.