DRASTIC EFFECTS OF DIOXYGEN ON THE SELECTIVITY OF REDUCTION BY LIALH4- MILDER CONDITIONS MADE POSSIBLE BY STRICTLY ANAEROBIC CONDITIONS

Authors
PERALEZ E NEGREL JC CHANON M
Citation
E. Peralez et al., DRASTIC EFFECTS OF DIOXYGEN ON THE SELECTIVITY OF REDUCTION BY LIALH4- MILDER CONDITIONS MADE POSSIBLE BY STRICTLY ANAEROBIC CONDITIONS, Tetrahedron letters, 36(36), 1995, pp. 6457-6460
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
36
Year of publication
1995
Pages
6457 - 6460
Database
ISI
SICI code
0040-4039(1995)36:36<6457:DEODOT>2.0.ZU;2-1
Abstract
Reduction of the gem-disubstituted cyclopropane 1 with LiAlH4 yields d ifferent results under strictly anaerobic conditions and loosely anaer obic ones. Under strictly anaerobic conditions, (+)-1-bromo-2,2-diphen ylcyclopropanecarbinol 2 is quantitatively reduced to 3 with complete racemization. These observations are explained by a radical chain mech anism. They open the way to reductions by LiAlH4 under mild conditions .