62872-79-1Relevant academic research and scientific papers
PREPARATION AND NUCLEOPHILIC SUBSTITUTION OF (E)-1-BROMO-2-PHENYLSULFONYL-2-ALKENES AND 3-ACETOXY-2-PHENYLSULFONYL-1-ALKENES
Auvray, P.,Knochel, P.,Normant, J. F.
, p. 6095 - 6106 (2007/10/02)
Vinylphenylsulfone reacts with aldehydes to yield sulfonylated secondary allylic alcohols wich are converted to either primary allylic bromides, or secondary allylic acetates.Both react highly regioselectively with lithium cyanocuprates, or enolates.
AN EASY SYNTHESIS OF THE 2-PHENYLSULFONYL-SUBSTITUTED ALLYLIC BROMIDES AND ACETATES AND THEIR REACTIVITY TOWARDS NUCLEOPHILES
Auvray, P.,Knochel, P.,Normant, J. F.
, p. 5095 - 5098 (2007/10/02)
The reaction of phenyl vinyl sulfone with various aldehydes in the presence of a catalytic amount of DABCO furnishes in good yields the corresponding 2-phenylsulfonyl-substituted alcohols 5a-5e which can be easily converted into their acetates 2a-2b or into their allylically rearranged bromides 3a-3d.These reagents, in turn, react with nucleophiles (ketone enolates and cuprates) with an allylic rearrangement (SN2' mechanism) to give the functionalized unsaturated sulfones 6a-g and 7a-g.A palladium catalyzed reaction allows a stereo-controlled transformation of the sulfone 6b into the (Z,Z) skipped 1,4-diene 8.
Selective alkylation of allyl phenyl sulphone. A novel synthesis of alk-2-enes
Savoia, Diego,Trombini, Claudio,Umani-Ronchi, Achille
, p. 123 - 125 (2007/10/12)
Treatment of the lithium salt of allyl phenyl sulphone (1) with a variety of alkyl halides affords exclusively α-alkylated products (2a-d). which are easily isomerized to (E)-αβ-unsaturated phenyl sulphones (4a-d) with catalytic amounts of t-butoxide. A new, simple method of reductive cleavage of the carbon-sulphur bonds of compounds (2)-(4) with potassium-graphite (C8K) is described, providing a general route to alk-2-enes [(5) and (6)] in satisfactory yields.
