85185-31-5Relevant academic research and scientific papers
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.
