Preparation of α-(2,2-diphenylhydrazino)- and α-(benzyloxyamino)-lactones by radical cyclization: use of glyoxylic acid diphenylhydrazone and glyoxylic acid O-benzyloxime

Autor: L. J. Clive, Derrick, Zhang, Junhu
Zdroj: Chemical Communications; March 21, 1997, Vol. 1997 Issue: 6 p549-550, 2p
Abstrakt: Glyoxylic acid diphenylhydrazone (2, Y = NPh2) and the corresponding O-benzyloxime (2, Y = OBn) are easily esterified in high yield by β-bromo alcohols, and the resulting esters undergo radical cyclization to α-(2,2-diphenylhydrazino) or α-(benzyloxyamino) lactones on treatment with tributyltin hydride; the initial radical can be formed by homolysis of a carbon–selenium bond as well as a carbon–bromine bond and, when applied to appropriate alcohols, the esterification–radical closure sequence can also be used to make six- or seven-membered lactones.
Databáze: Supplemental Index