A DIQUINANE SYNTHESIS USING A NOVEL CATION RADICAL-MEDIATED INTRAMOLECULAR [3+2] CYCLOADDITION OF CYCLOPROPYL SULFIDES

Authors
TAKEMOTO Y FURUSE S KOIKE H OHRA T IWATA C OHISHI H
Citation
Y. Takemoto et al., A DIQUINANE SYNTHESIS USING A NOVEL CATION RADICAL-MEDIATED INTRAMOLECULAR [3+2] CYCLOADDITION OF CYCLOPROPYL SULFIDES, Tetrahedron letters, 36(23), 1995, pp. 4085-4088
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
23
Year of publication
1995
Pages
4085 - 4088
Database
ISI
SICI code
0040-4039(1995)36:23<4085:ADSUAN>2.0.ZU;2-Y
Abstract
Cyclopropyl sulfides 2 bearing a benzylidene moiety are effectively tr ansformed into diquinanes by treatment with tris-(4-bromophenyl)aminiu m hexachloroantimonate, as a single-electron oxidant, in dichlorometha ne at room temperature. This [3+2] cycloaddition reaction requires ben zylidene moieties as a C-C double bond component.