CHEMOSELECTIVITY OF RHODIUM CARBENOIDS - A COMPARISON OF THE SELECTIVITY FOR O-H INSERTION REACTIONS OR CARBONYL YLIDE FORMATION VERSUS ALIPHATIC AND AROMATIC C-H INSERTION AND CYCLOPROPANATION

Authors
COX GG MOODY CJ AUSTIN DJ PADWA A
Citation
Gg. Cox et al., CHEMOSELECTIVITY OF RHODIUM CARBENOIDS - A COMPARISON OF THE SELECTIVITY FOR O-H INSERTION REACTIONS OR CARBONYL YLIDE FORMATION VERSUS ALIPHATIC AND AROMATIC C-H INSERTION AND CYCLOPROPANATION, Tetrahedron, 49(23), 1993, pp. 5109-5126
Citations number
50
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
23
Year of publication
1993
Pages
5109 - 5126
Database
ISI
SICI code
0040-4020(1993)49:23<5109:CORC-A>2.0.ZU;2-L
Abstract
A range of diazocarbonyl compounds 1-9 containing two different functi onal groups has been prepared, and their rhodium(II) catalysed decompo sition studied as a means of probing the chemoselectivity of carbenoid intermediates. The results indicate that whereas O-H insertion reacti ons predominate over cyclopropanation and aromatic insertion reactions , carbonyl ylide formation vs. other competing processes is more finel y balanced, and is catalyst dependent.