Novel ring transformation of dihydroselenines to selenabicyclo[3.1.0]hexenes

Authors
Honda, E Watanabe, S Iwamura, T Kataoka, T
Citation
E. Honda et al., Novel ring transformation of dihydroselenines to selenabicyclo[3.1.0]hexenes, HETEROCYCLE, 55(3), 2001, pp. 465-468
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
3
Year of publication
2001
Pages
465 - 468
Database
ISI
SICI code
0385-5414(20010301)55:3<465:NRTODT>2.0.ZU;2-5
Abstract
Treatment of 2-bromo-2,6-dicyano-2,3-dihydroselenine (6) with triethylamine in ethanol gave 2-selenabicyclo[3.1.0]hex-3-ene (7) in 77% yield. Reaction of 7 with benzyne formed benzoselenophene (II) in 35% yield. Methylation o f 7 with methyl triflate produced Se-methylselenonium salt (12), which was transformed into amide derivatives (16) and (17). Compound (7) was converte d into alkynylcyclopropane (13) via selenonium salt (12).