REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OFCHELATING PROCESSES .11. RING-OPENING REACTIONS OF ALIPHATIC MONOFUNCTIONALIZED AND DIFUNCTIONALIZED CIS AND TRANS 2,3-EPOXY AND 3,4-EPOXY ESTERS

Authors
AZZENA F CROTTI P FAVERO L PINESCHI M
Citation
F. Azzena et al., REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OFCHELATING PROCESSES .11. RING-OPENING REACTIONS OF ALIPHATIC MONOFUNCTIONALIZED AND DIFUNCTIONALIZED CIS AND TRANS 2,3-EPOXY AND 3,4-EPOXY ESTERS, Tetrahedron, 51(48), 1995, pp. 13409-13422
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
48
Year of publication
1995
Pages
13409 - 13422
Database
ISI
SICI code
0040-4020(1995)51:48<13409:RCOTRO>2.0.ZU;2-C
Abstract
The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidol ysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and i n the corresponding derivatives bearing an ether functionality (OBn) i n an allylic relationship to the oxirane ring. The results indicate th at the behavior of these epoxides is influenced both by the opening co nditions (standard or metal-assisted) and the promoting metal salt [Li ClO4 or Mg(ClO4)(2)].