MECHANISM OF P-QUINONE METHIDE INITIATED CYCLIZATION REACTIONS TERMINATED BY ALKENES - 1,2-HYDROGEN VS 1,3-HYDROGEN MIGRATION

Authors
ANGLE SR HOSSAIN MA
Citation
Sr. Angle et Ma. Hossain, MECHANISM OF P-QUINONE METHIDE INITIATED CYCLIZATION REACTIONS TERMINATED BY ALKENES - 1,2-HYDROGEN VS 1,3-HYDROGEN MIGRATION, Tetrahedron letters, 35(26), 1994, pp. 4519-4522
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
26
Year of publication
1994
Pages
4519 - 4522
Database
ISI
SICI code
0040-4039(1994)35:26<4519:MOPMIC>2.0.ZU;2-B
Abstract
Intramolecular cyclization of benzylic cations derived from p-quinone methides 5 and 6, afforded the corresponding six- or seven-membered ri ng products 7 or 9 depending on the substitution of the alkene. Deuter ium labeling experiments indicated that formation of 9 occurred via a 1,3-hydrogen shift, whereas formation of 7 proceeded via two sequentia l 1,2-hydride transfers.