Health & Environmental Research Online (HERO)


Print Feedback Export to File
6678696 
Journal Article 
PHENYLTHIO (AND PHENYLSELENO)FLUORINATION OF ALKENES AND ALKENES USING N-PHENYLTHIO (AND PHENYLSELENO)PHTHALIMIDE COMBINED WITH PYRIDINE-9HF OR ET3N-3HF COMPLEXES 
Saluzzo, C; Laspina, AM; Picq, D; Alvernhe, G; Anker, D; Wolf, D; Haufe, G; , 
1994 
Yes 
Bulletin de la Société Chimique de Paris
ISSN: 0037-8968 
EDITIONS SCIENTIFIQUES ELSEVIER 
PARIS CEDEX 15 
831-843 
WOS:A1994PW53000006 
Phenylthio (and phenylseleno)fluorination of alkenes and alkynes using N-phenylthio (and phenylseleno)phthalimide combined with pyridine . 9HF or Et3N . 3HF complexes. N-Phenylthiophthalimide and N-phenylselenophthalimide combined with pyridine . 9HF and Et3N . 3HF complexes allow the formal addition of elements of PhSF or PhSeF across the carbon-carbon double or triple bond by a one-pot reaction. Pyridine . 9HF, a strongly acidic reagent, is required to polarize the S-N bond and, therefore, gives rise to some by-products. In contrast, selenium-containing compounds are obtained in good yields using the less acidic Et3N . 3HF complex avoiding cleavage of acetals or isomerization; the formal PhSeF addition is totally regioselective with propargylic alcohols.