Preparation of α-(2,2-diphenylhydrazino)- and α-(benzyloxyamino)-lactones by radical cyclization: use of glyoxylic acid diphenylhydrazone and glyoxylic acid O-benzyloxime
- 1 January 1997
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 6,p. 549-550
- https://doi.org/10.1039/a608236j
Abstract
Glyoxylic acid diphenylhydrazone (2, Y = NPh 2 ) 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.Keywords
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