IODINE-INDUCED TRANSANNULAR COUPLING OF 1,6-CYCLODECADIYNE

Authors
GU XH SPONSLER MB
Citation
Xh. Gu et Mb. Sponsler, IODINE-INDUCED TRANSANNULAR COUPLING OF 1,6-CYCLODECADIYNE, Tetrahedron letters, 37(10), 1996, pp. 1571-1574
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
10
Year of publication
1996
Pages
1571 - 1574
Database
ISI
SICI code
0040-4039(1996)37:10<1571:ITCO1>2.0.ZU;2-W
Abstract
Treatment of 1,6-cyclodecadiyne (1) with one equivalent of iodine in e ther leads to regioselective transannular coupling, producing 1,5-diio do-2,3,4,6,7,8-hexahydronaphthal (2) in excellent yield. Solvent-incor poration products are observed in addition to 2 when the reaction is d one in benzene, chlorobenzene, or methanol. Bromination of 1 gives ana logous products, but the reaction is not as clean.