STEREOCHEMISTRY OF THE ADDITION PRODUCT OF N-AMINOSUCCINIMIDE MOIETY TO AN ACETYLENIC ESTER

Citation
A. Srivastava et al., STEREOCHEMISTRY OF THE ADDITION PRODUCT OF N-AMINOSUCCINIMIDE MOIETY TO AN ACETYLENIC ESTER, Bulletin of the Chemical Society of Japan, 67(5), 1994, pp. 1386-1389
Citations number
19
Categorie Soggetti
Chemistry
ISSN journal
00092673
Volume
67
Issue
5
Year of publication
1994
Pages
1386 - 1389
Database
ISI
SICI code
0009-2673(1994)67:5<1386:SOTAPO>2.0.ZU;2-B
Abstract
H-1, C-13 NMR and X-ray crystallography have demonstrated the azomethi ne structure of the addition product obtained from -2,3-(9,10-dihydro- 9,10-anthracenediyl)succinimide and diethyl acetylenedicarboxylate. Th e exo cyclic nitrogen exists in sp2-state and its lone pair lies in an ti orientation while the diethyl succinate moiety has been demonstrate d to be syn to the cage and orthogonal to the succinimide plane. On ac etylation the product is transformed into N-acetyl derivative which ex hibits restricted rotation about N-N bond and a preferred conformation with N-acetyl in syn-orientation.