AN INTERPLAY IN THE REGIOSELECTIVITY INDUCED BY NON BONDING INTERACTIONS, IN THE ENE REACTIONS OF SINGLET OXYGEN AND TRIAZOLINEDIONES WITH TETRASUBSTITUTED ALKENES

Authors
ELEMES Y STRATAKIS M ORFANOPOULOS M
Citation
Y. Elemes et al., AN INTERPLAY IN THE REGIOSELECTIVITY INDUCED BY NON BONDING INTERACTIONS, IN THE ENE REACTIONS OF SINGLET OXYGEN AND TRIAZOLINEDIONES WITH TETRASUBSTITUTED ALKENES, Tetrahedron letters, 38(36), 1997, pp. 6437-6440
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
36
Year of publication
1997
Pages
6437 - 6440
Database
ISI
SICI code
0040-4039(1997)38:36<6437:AIITRI>2.0.ZU;2-F
Abstract
The ene reactions of N-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and si nglet oxygen (O-1(2)) with tetrasubstituted alkenes, follow regioselec tivity trends governed mainly by 1,3-non bonded interactions (type I) for the case of PTAD, and mainly by the steric hindrance caused during the formation of the new double bond (type II) for the case of O-1(2) . The results are explained hi terms of a ''late'' product forming tra nsition state of hydrogen abstraction for triazolinediones and an ''ea rly'' transition st;lte for the analogous singlet oxygen reaction. (C) 1997 Elsevier Science Ltd.