DIHYDROFURANS FROM ALPHA-DIAZOKETONES - FACILE REARRANGEMENT OF DONOR-ACCEPTOR CYCLOPROPANES

Authors
LUND EA KENNEDY IA FALLIS AG
Citation
Ea. Lund et al., DIHYDROFURANS FROM ALPHA-DIAZOKETONES - FACILE REARRANGEMENT OF DONOR-ACCEPTOR CYCLOPROPANES, Tetrahedron letters, 34(43), 1993, pp. 6841-6844
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
43
Year of publication
1993
Pages
6841 - 6844
Database
ISI
SICI code
0040-4039(1993)34:43<6841:DFA-FR>2.0.ZU;2-G
Abstract
The direct synthesis of dihydrofurans 7, 1 1, and 23- 25 from alpha-di azoketones 3, 8, and 20-22 is described. The cyclopropane intermediate s generated upon treatment of the alpha-diazoketones with metal cataly sts in the presence of ethyl vinyl ether rearranged spontaneously. Sen sitized irradiation of 3 afforded 7 plus cyclobutanone 5 while direct photolysis gave the cyclobutanones 5. and 26-28.