Citation
Jd. Kim et al., Novel synthetic method for N-allylcarbamates from allyl ethers using chlorosulfonyl isocyanate, TETRAHEDR L, 41(26), 2000, pp. 5073-5076
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039
→ ACNP
Volume
41
Issue
26
Year of publication
2000
Pages
5073 - 5076
Database
ISI
SICI code
0040-4039(20000624)41:26<5073:NSMFNF>2.0.ZU;2-E
Abstract
Various allyl ethers were converted into the corresponding N-allylcarbamate
s using chlorosulfonyl isocyanate (CSI) via the stable allylic carbocation
rather than beta-lactam through [2+2] cycloaddition. The reaction of cinnam
yl methyl ether with CSI afforded only methyl N-cinnamyloarbamate at 0 degr
ees C, but at 20 degrees C, it produced a mixture of methyl N-cinnamylcarba
mate and methyl N-(1-phenylprop-2-enyl)carbamate in a 2.7:1 ratio. (C) 2000
Elsevier Science Ltd. All rights reserved.