Reduction of cyclic anhydrides. II. Factors affecting regioselectivity of attack on the carbonyl group by metal hydrides
- 1 June 1978
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 56 (11), 1524-1532
- https://doi.org/10.1139/v78-247
Abstract
The reduction of unsymmetrically substituted cyclic anhydrides with metal hydrides often leads to the preferential formation of one of the two possible lactones. In the light of recent experimental findings and theories concerning metal hydride addition to the carbonyl function, the electronic and steric factors influencing regioselectivity of cyclic anhydride reductions are discussed and an explanation for the observed patterns is proffered. Similar considerations may be extended to predict the major lactonic products in the reductions of various other unsymmetrical cyclic anhydrides.This publication has 1 reference indexed in Scilit:
- Einwirkung des Caro'schen Reagens auf KetoneEuropean Journal of Inorganic Chemistry, 1899