SEDUCTIVE CLEAVAGE AND RING EXPANSION OF THIOCHROMANE AND BENZODIHYDROTHIOPHENE

Authors
COHEN T CHEN FP KULINSKI T FLORIO S CAPRIATI V
Citation
T. Cohen et al., SEDUCTIVE CLEAVAGE AND RING EXPANSION OF THIOCHROMANE AND BENZODIHYDROTHIOPHENE, Tetrahedron letters, 36(25), 1995, pp. 4459-4462
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
25
Year of publication
1995
Pages
4459 - 4462
Database
ISI
SICI code
0040-4039(1995)36:25<4459:SCAREO>2.0.ZU;2-Y
Abstract
Reductive ring cleavage of thiochromane and benzodihydrothiophene by t he radical-anion 4,4'-di-tert-butylbiphenylide (LDBB) leads to organol ithium compounds bearing a lithium arylthiolate group. The adducts of the latter with aldehydes and ketones undergo ring closure when treate d under appropriate acidic conditions. The result is a two-pot one-car bon substitutive ring expansion of the original sulfur heterocycle.