90838-48-5Relevant academic research and scientific papers
The stereospecific synthesis of cis and trans 1-oxabicyclo[4,4,0]decanes and 9-methoxycarbonyl-1-oxabicyclo[4,3,0] nonanes
Jones, D. Neville,Khan, M. Akram,Mirza, Sohail M.
, p. 9933 - 9946 (2007/10/03)
The allylic sulphoxides 1b and 1e reacted with 1- pyrrolidinylcyclohexene and 2-ethoxycarbonyl cyclopentanone to yield the 2- substituted keto-sulphoxides 10 and 14 respectively, which on reduction followed by oxidation yielded in each case a mixture of cis and trans sulphones that were separated by column chromatography. Base induced cyclisation followed by reductive desulphurisation of the cyclised sulphones yielded the corresponding bicyclic compounds 6, 7, 8 and 9 in good yields.
3-Chloro-2-(phenylsulfinyl)-1-propene and 3-Chloro-2-(phenylsulfonyl)-1-propene: Preparation and Utility as Reagents for α,α'-Annelation of Cyclic Ketones
Anzeveno, Peter B.,Matthews, Donald P.,Barney, Charlotte L.,Barbuch, Robert J.
, p. 3134 - 3138 (2007/10/02)
The reaction of allyl chloride (7), at -40 deg C to -20 deg C, with in situ generated phenylsulfenyl chloride (6) affords exclusively the anti-Markovnikov product 1,3-dichloro-2-(phenylthio)propane (8) in 85-90percent yield.Oxidation of 8 with 1 equiv of MCPBA to sulfoxide 9 followed by DBU-catalyzed dehydrochlorination yields 3-chloro-2-(phenylsulfinyl)-1-propene (1d) (70percent).Treatment of 8 with 2 equiv of MCPBA yields sulfone 10 which is similarly dehydrochlorinated to 3-chloro-2-(phenylsulfonyl)-1-propene (1e)(81percent).The reaction of pyrrolidine enamines of cyclic ketones with 1d and 1.1 equiv of triethylamine in Me2SO at 95-100 deg C affords moderate yields of bicyclic keto thioenol ethers, formed via an α,α'-annelation-Pummerer reaction sequence, together with noncyclized, 2-(phenylsulfinyl)allylated ketone.Similar reactions with 1e provide good yields of bicyclic keto sulfones as approximate 1:1 mixtures of endo and exo isomers, which may be equilibrated to mixtures containing predominantly the exo compounds by treatment with methanolic sodium methoxide.
