98506-80-0Relevant articles and documents
A new synthesis of α-fluorovinylsulfones utilizing the Peterson olefination methodology
Asakura, Noriaki,Usuki, Yoshinosuke,Iio, Hideo
, p. 81 - 88 (2007/10/03)
α-Fluoro-α-silyl-substituted sulfones 1 are readily prepared from fluoromethyl phenyl sulfone and the appropriate silyl chloride. The use of TBSCl improves both the stability and yield of 1. Lithium derivatives 4 undergo a smooth Peterson olefination reaction with less-enolizable carbonyl compounds to give moderate to good yields of the expected α-fluorovinylsulfones 6, in some cases with high E-stereoselectivity. One-pot reaction with 4 generated in situ from fluoromethyl phenyl sulfone in tetrahydrofuran (THF) also proceeds smoothly, particularly with aldehydes.
Stereospecific synthesis of 1-fluoro olefins via (fluoro-vinyl)stannanes and an unequivocal NMR method for the assignment of fluoro olefin geometry
McCarthy,Huber,Le,Laskovics,Matthews
, p. 45 - 58 (2007/10/02)
(E)- and (Z)-Fluorovinyl sulfones (II) form (fluorovinyl)stannanes (III) on treatment with two equivalents of tributyltin hydride and a catalytic amount of AIBN; the free radical catalyzed reaction proceeds with retention of configuration for 2,2-disubstituted fluorovinyl sulfones (IIa and IIb). Conversion of III to 1-fluoro olefins (IV) is a stereospecific reaction and provides a general method to (E) and (Z) fluoro olefins. The utility of this method is exemplified by the synthesis of the deutero fluoro olefins 27, nucleosides 32 and 34, and the amino acids 43 and 47. Proton observe, 19F irradiated (1H-{19F}) NOE difference spectroscopy was used for the first time as an unequivocal method for the assignment of olefin geometry for fluorovinyl sulfones, (fluorovinyl)stannanes and fluoro olefins.
A new route to vinyl fluorides
McCarthy,Matthews,Edwards,Stemerick,Jarvi
, p. 5449 - 5452 (2007/10/02)
The carbanion of diethyl 1-fluoro-1-(phenylsulfonyl)methanephosphonate (7), generated in situ from fluoromethyl phenyl sulfone (3) undergoes the Horner-Wittig reaction with aldehydes and ketones to yield α-fluoro-α,β-unsaturated sulfones (8). Reductive re
A Novel and Efficient Synthesis of Fluoromethyl Phenyl Sulphone and Its Use as a Fluoromethyl Wittig Equivalent
Inbasekaran, Muthiah,Peet, Norton P.,McCarthy James R.,LeTourneau, Michael E.
, p. 678 - 679 (2007/10/02)
A new synthesis of fluoromethyl phenyl sulphone (2) and the reaction of its conjugate base (3) with carbonyl compounds provides β-fluoro-alcohols (5), which are utilized to prepare terminal vinyl fluorides (8) via α-fluoro-α,β-unsaturated sulphones (6).
