ON THE MECHANISM OF ACID-PROMOTED RING-OPENING OF A .4.0.0(2,6).0(3,10).0(5,9)]UNDECANE-SPIROANNULATED OXETANE

Authors
MARCHAND AP WANG YJ REN CT VIDYASAGAR V WANG DQ
Citation
Ap. Marchand et al., ON THE MECHANISM OF ACID-PROMOTED RING-OPENING OF A .4.0.0(2,6).0(3,10).0(5,9)]UNDECANE-SPIROANNULATED OXETANE, Tetrahedron, 52(17), 1996, pp. 6063-6072
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
17
Year of publication
1996
Pages
6063 - 6072
Database
ISI
SICI code
0040-4020(1996)52:17<6063:OTMOAR>2.0.ZU;2-J
Abstract
Specifically deuterated cage-spiroannulated oxetanes 1a and 1b each un dergo ring opening with concomitant skeletal rearrangement when heated with glacial HOAc in the presence of a catalytic amount of concentrat ed H2SO4. The fate of the deuterium atom in each substrate, as determi ned via analysis of the NMR spectra of the rearrangement products, est ablishes unequivocally that a key step in this process proceeds via hi ghly stereoselective intramolecular 1,5-hydride transfer. (C) 1996 Els evier Science Ltd.