ANTI CIS EFFECT SELECTIVITY IN THE REACTION OF SINGLET OXYGEN WITH TRISUBSTITUTED ALKENES

Authors
STRATAKIS M ORFANOPOULOS M
Citation
M. Stratakis et M. Orfanopoulos, ANTI CIS EFFECT SELECTIVITY IN THE REACTION OF SINGLET OXYGEN WITH TRISUBSTITUTED ALKENES, Tetrahedron letters, 36(24), 1995, pp. 4291-4294
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
24
Year of publication
1995
Pages
4291 - 4294
Database
ISI
SICI code
0040-4039(1995)36:24<4291:ACESIT>2.0.ZU;2-R
Abstract
In the reaction of singlet oxygen with certain trisubstituted alkenes, a strong preference for regioselectivity favoring hydrogen abstractio n on that side of the olefin with one substituent has been recognized. These results are rationalized in terms of non bonded interactions an d the lack of oxygen interaction with two allylic hydrogens in the sam e side of the double bond.