85185-32-6Relevant academic research and scientific papers
A sulfoxide version of the Julia-Lythgoe olefination: A new method for the synthesis of olefins from carbonyl compounds and sulfoxides with carbon-carbon coupling
Satoh, Tsuyoshi,Hanaki, Noriko,Yamada, Noriko,Asano, Tohru
, p. 6223 - 6234 (2007/10/03)
Reaction of β-mesyloxy (or acetoxy) sulfoxides, derived from alkyl (or arylmethyl) phenyl sulfoxides and carbonyl compounds in two steps, with alkylmetals (n-BuLi, t-BuLi, or EtMgBr) at low temperature gave olefins in good to excellent yields. When the β-hydroxy sulfoxides derived from arylaldehydes were treated with mesyl chloride in the presence of triethylamine, the sulfoxides directly gave E-olefins in good yields. These reactions offer a sulfoxide version of the Julia-Lythgoe olefination. The reductive vicinal elimination was found to take place through the direct sulfoxide-metal exchange. The stereochemistry of the elimination was investigated and found to be stereospecific; however, the stereospecificity was found to be dependent on the substrates. (C) 2000 Elsevier Science Ltd.
Ligand exchange reaction of sulfoxides in organic synthesis: Sulfoxide version of the Julia-Lythgoe olefination
Satoh, Tsuyoshi,Yamada, Noriko,Asano, Tohru
, p. 6935 - 6938 (2007/10/03)
Reaction of β-mesyloxy sulfoxides, derived from alkyl (or arylmethyl) phenyl sulfoxides and aldehydes in two steps, with alkylmetal (n-BuLi, t- BuLi, or EtMgBr) at -78°C gave olefins in good to excellent yields. This reaction offers a sulfoxide version of the Julia-Lythgoe olefination.
A New Synthesis of Olefins via the Elimination Reaction of β-Tributylstannyl Organosulfur Compounds
Ochiai, Masahito,Ukita, Tatsuzo,Fujita, Eiichi,Tada, Shin-ichi
, p. 1829 - 1839 (2007/10/02)
Organosulfur compounds on treatment with butyllithium in tetrahydrofuran followed by tributylstannylmethyl iodide 1 afforded olefins.The reaction was found to proceed via the destannylsulfurization of the initially formed β-stannyl organosulfur compounds.Thus, allyl 2-pyridyl sulfides 2 or allyl phenyl sulfones 12 were converted into 1,3-dienes 4.Compounds 13 and 15 were converted into the olefins 14 and 17.Furthermore, the reaction was applied to the synthesis of α-substituted vinyl sulfides 24 and allene 27.The stereochemistry of the double bond is discussed.Keywords - destannylsulfurization; allyl 2-pyridyl sulfide; allyl phenyl sulfone; synthesis of olefin; 1,3-diene; vinyl sulfide; β-tributylstannyl organosulfur compound.
Synthesis of the Aryltetralin Lignan Skeleton via the Prins Reaction
Snider, Barry B.,Jackson, Andrew C.
, p. 1471 - 1474 (2007/10/02)
Reaction of a 1,4-diaryl-1-butene (7) with paraformaldehyde and the appropriate alkylaluminum halide generates the cation 8, via addition of formaldehyde to the double bond, which cyclizes to give the aryltetralin 9.Reaction of 1,4-diphenyl-2-butene (6a) with paraformaldehyde and methylaluminum sesquichloride gives the ene adduct 5a, which reacts further, analogously to 7, to give 4a which possesses the aryltetralin lignan skeleton.
