42104-21-2Relevant academic research and scientific papers
"Syn-Effect" in the Conversion of (E)-Vinylic Sulfones to the Corresponding Allylic Sulfones
Hirata, Takaki,Sasada, Yoshihiro,Ohtani, Takashi,Asada, Takahiro,Kinoshita, Hideki,et al.
, p. 75 - 96 (2007/10/02)
It was found that (E)-vinylic sulfones preferentially afford (Z)-allylic sulfones as kinetically-controlled products by treatment with a base under mild conditions, while (Z)-vinylic sulfones give (E)-allylic sulfones.Such stereochemical relationship was
Synthetic Studies on Electron Transport Inhibitors. Part 1. Chiral Synthesis of a Synthon for Myxalamide D, Piericidin A, and the Actinopyrones
Cox, Catherine M.,Whiting, Donald A.
, p. 1901 - 1905 (2007/10/02)
The trimethylsilyl enolate 9 of (1'R,2'S)-N-methylephedrine propionate was condensed with tiglic aldehyde to afford the (1'R,2'S,2S,3R)-ester 10 with high stereoselectivity; conversion into the aldehyde 12 was effected without epimerization, and the seque
A 1,3-Rearrangement of Allylic Sulphones Caused by m-Chloroperbenzoic Acid and Sodium Hydrogen Carbonate
Kocienski, Philip
, p. 945 - 948 (2007/10/02)
The reaction of allylic sulphones with m-chloroperbenzoic acid in the presence of aqueous sodium hydrogen carbonate can result in 1,3-allylic rearrangement or isomerisation of the double bond depending on the structure of the allylic sulphone.Subsequent e
The Influence of Chain-branching on the Steric Outcome of Some Olefin-forming Reactions
Kocienski, Philip J.,Lythgoe, Basil,Waterhouse, Ian
, p. 1045 - 1050 (2007/10/02)
When applied to the construction of internal disubstituted double bonds in compounds such as pentadec-7-ene and 2,6,11,15-tetramethylhexadeca-2,6,8,10,14-pentaene (5), the reductive elimination of vicinal benzoyloxy-sulphones gives products with a trans:cis ratio of ca. 4:1.When applied to the construction of disubstituted olefins in which branching occurs adjacent to the newly formed double bond, much higher trans-stereoselectivity is observed, e.g. for 5-ethyl-2-methylhept-3-ene (21) and 3,6-dimethylocta-2,4,6-triene (25) it is at least 98percent.A similar effect of chain-branching is also observed in some Wittig and Horner reactions using primary allylic phosphorus derivatives.When a Z-allylic sulphone is used as the starting material in the benzoyloxy-sulphone method, the original Z-geometry is preserved in the product; (Z)-2-methylbut-2-enyl p-tolyl sulphone and tiglic aldehyde give almost exclusively (2E,4E,6Z)-3,6-dimethylocta-2,4,6-triene (27).
