THE RHODIUM(II) ACETATE-CATALYZED REACTION OF ALKENYL AND ALKYNYL ALPHA-DIAZOACETATES WITH THIOKETENE

Authors
NAKANO H IBATA T
Citation
H. Nakano et T. Ibata, THE RHODIUM(II) ACETATE-CATALYZED REACTION OF ALKENYL AND ALKYNYL ALPHA-DIAZOACETATES WITH THIOKETENE, Bulletin of the Chemical Society of Japan, 68(5), 1995, pp. 1393-1400
Citations number
20
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
68
Issue
5
Year of publication
1995
Pages
1393 - 1400
Database
ISI
SICI code
0009-2673(1995)68:5<1393:TRAROA>2.0.ZU;2-8
Abstract
The reaction of allyl alpha-diazoacetates with di-t-butylthioketene ca talyzed by Rh-2(OAc)(4) gave 4-allyl-2-methylene-1,3-oxathiolan-5-ones through the 1,5-cyclization of a thiocarbonyl ylide intermediate foll owed by Claisen rearrangement with allene episulfide through the 1,3-c yclization of the intermediate. Other alkenyl and alkynyl diazoacetate s also gave similar products through the thiocarbonyl ylide without af fording its intramolecular 1,3-dipolar cycloadduct.