SELECTIVE THIOPHILIC ADDITION OF ALKYLLITHIUM AND ARYLLITHIUMS TO DITHIO ESTERS AND A SULFINE IN THE PYRIDINE SERIES

Authors
LEMPEREUR C PLE N TURCK A QUEGUINER G CORBIN F ALAYRAC C METZNER P
Citation
C. Lempereur et al., SELECTIVE THIOPHILIC ADDITION OF ALKYLLITHIUM AND ARYLLITHIUMS TO DITHIO ESTERS AND A SULFINE IN THE PYRIDINE SERIES, Heterocycles, 48(10), 1998, pp. 2019-2034
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
48
Issue
10
Year of publication
1998
Pages
2019 - 2034
Database
ISI
SICI code
0385-5414(1998)48:10<2019:STAOAA>2.0.ZU;2-1
Abstract
Reaction of two dithio esters and a new sulfine (S-thiocarbonyl oxide) with various aryl- and alkyllithiums at -78 degrees C afforded dithio acetals or their oxides, arising from a thiophilic addition. The inte rmediate carbanions can be trapped by alkyl halides or an aldehyde. Th is provides a new entry to pyridyl acyl anions, ''Umpolung'' synthons.