1,3-DITHIENIUM AND 1,3-DITHIOLENIUM SALTS - IX - REACTIONS OF 1,3-DITHIANE-2-YLIUM TETRAFLUOROBORATES WITH C-NUCLEOPHILES

Citation
M. Linker et al., 1,3-DITHIENIUM AND 1,3-DITHIOLENIUM SALTS - IX - REACTIONS OF 1,3-DITHIANE-2-YLIUM TETRAFLUOROBORATES WITH C-NUCLEOPHILES, Journal fur praktische Chemie, Chemiker-Zeitung, 340(1), 1998, pp. 63-72
Citations number
48
Categorie Soggetti
Chemistry,"Chemistry Applied
ISSN journal
09411216
Volume
340
Issue
1
Year of publication
1998
Pages
63 - 72
Database
ISI
SICI code
0941-1216(1998)340:1<63:1A1S-I>2.0.ZU;2-5
Abstract
1,3-Dithian-2-ylium tetrafluoroborates (1), which can be easily obtain ed by variable methods, react in good to excellent yields with variabl e C-nucleophiles to new geminal disubstituted 1,3-dithianes. The latte r compounds are potential precursors of interesting synthetic building blocks. Reactions are described with 2-lithio-1,3-dithianes 2, sodium cyanide 4, sodium salts of the nitro alkanes 7 and CH-acids of the ty pe of the 1,3-dicarbonyl compounds 9. The reduction of 3-oxo-2(2-pheny l-1,3-dithian-2-yl)-ethoxybutanoat - following a diastereoselective pa thway - leads to the Cram product 11. Further presented is the crystal structure of 2-phenyl-1,3-dithiane-2-ylium tetrafluoroborate (1b).