55499-06-4Relevant academic research and scientific papers
Nickel-catalyzed cross-coupling reactions of alkyl aryl sulfides and alkenyl alkyl sulfides with alkyl grignard reagents using (Z)-3,3-dimethyl-1,2- bis(diphenylphosphino)but-1-ene as ligand
Kanemura, Shigenari,Kondoh, Azusa,Yorimitsu, Hideki,Oshima, Koichiro
scheme or table, p. 2659 - 2664 (2009/04/05)
A combination of nickel(II) acetylacetonate and (Z)-3,3-dimethyl-1,2- bis(diphenylphosphino)but-1-ene catalyzes cross-coupling reactions of alkyl aryl sulfides and alkenyl alkyl sulfides with alkyl Grignard reagents. Not only primary but also secondary alkyl Grignard reagents can be employed. Georg Thieme Verlag Stuttgart.
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).
