REARRANGEMENT PATHWAYS OF THE TRICYCLO[4.1.0.0(1,3)]HEPTYL SKELETON

Authors
DOMBROWSKI GW GASSMAN PG KASS SR
Citation
Gw. Dombrowski et al., REARRANGEMENT PATHWAYS OF THE TRICYCLO[4.1.0.0(1,3)]HEPTYL SKELETON, Tetrahedron letters, 38(45), 1997, pp. 7819-7822
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
45
Year of publication
1997
Pages
7819 - 7822
Database
ISI
SICI code
0040-4039(1997)38:45<7819:RPOTTS>2.0.ZU;2-C
Abstract
Syn- and anti-1-methyltricyclo[4.1.0.0(4,6)]heptan-2-ol derivatives (4 a and 4b) have been prepared. Their buffered solvolyses in anhydrous 2 ,2,2-trifluoroethanol were studied. Anti dinitrobenzoate 4a solvolyzes to give mainly m-xylene and two trifluoroethyl ethers (5 and 6). Solv olysis of the syn mesylate 4b gives ,2,2-trifluoroethoxy)tricyclo[4.1. 0.0(3,5)]heptane (7). the product of a solvent trapped cyclopropyl cat ion. (C) 1997 Elsevier Science Ltd.