FACTORS WHICH CONTROL PI-FACIAL SELECTION IN THE REDUCTION OF 5-SUBSTITUTED ADAMANTANONES

Authors
COXON JM HOUK KN LUIBRAND RT
Citation
Jm. Coxon et al., FACTORS WHICH CONTROL PI-FACIAL SELECTION IN THE REDUCTION OF 5-SUBSTITUTED ADAMANTANONES, Journal of organic chemistry, 60(2), 1995, pp. 418-427
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
2
Year of publication
1995
Pages
418 - 427
Database
ISI
SICI code
0022-3263(1995)60:2<418:FWCPSI>2.0.ZU;2-S
Abstract
Ab initio and semiempirical calculations of the transition states for reduction of 5-substituted adamantanones with AlH3 show bond lengtheni ng and molecular orbitals consistent with hyperconjugative stabilizati on. Electronic as well as torsional effects contribute to facial selec tion.