A COMPARISON OF SUBSTITUENT FIELD EFFECTS ON THE REGIOCHEMISTRY OF THE ENE REACTIONS OF ALLYLIC SULFIDES AND ETHERS

Authors
CLENNAN EL KOOLA JJ CHEN MF
Citation
El. Clennan et al., A COMPARISON OF SUBSTITUENT FIELD EFFECTS ON THE REGIOCHEMISTRY OF THE ENE REACTIONS OF ALLYLIC SULFIDES AND ETHERS, Tetrahedron, 50(29), 1994, pp. 8569-8578
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
29
Year of publication
1994
Pages
8569 - 8578
Database
ISI
SICI code
0040-4020(1994)50:29<8569:ACOSFE>2.0.ZU;2-E
Abstract
The reactions of 4-methyl-1,2,4-triazolinedione with allylic ethers an d sulfides have been examined. The different responses of the regioche mistry in the two reaction series to changes in the electronic charact er of the substituents is attributed to the difference in the C-S (1.8 2 Angstrom) and C-O (1.43 Angstrom) bond lengths and/or the larger van der Waals radius of sulfur in comparison to oxygen.