77548-22-2Relevant academic research and scientific papers
REGIOSELECTIVITY IN THE REACTION OF CYCLOPENTENONES WITH CARBAIONS OF PHENYL ALLYL SULFIDE, SULFOXIDE, AND SULFONE
Vasil'eva, L. L.,Mel'nikova, V. I.,Gainullina, E. T.,Pivnitskii, K. K.
, p. 835 - 843 (2007/10/02)
The condensation of allylic carbanion of phenyl allyl sulfide, sulfoxide, and sulfone with 2-cyclopenten-1-one takes place by mechanisms of 1,2-addition and regioselective and nonregioselective 1,4-addition respectively.The reaction of phenyl allyl sulfone anion gives the 1,4-γ-adduct preferentially in the case of the lithium counterion and the 1,4-α-adduct with the potassium counterion.The 1,4-γ-addition of the phenyl allyl sulfoxide anion to 2-cyclopenten-1-one is characterized by full stereoselectivity, which also remains during the condensations of the phenyl1-vinylhexyl sulfoxide anion and 4-(1-methyl-1-phenylethoxy)-2-cyclopenten-1-one (prostaglandin synthons).
HMPA-MEDIATED CONJUGATE ADDITION OF ALKYL- AND PHENYLTHIOALLYL ANIONS TO CYCLOPENTENONE
Binns, Malcolm R.,Haynes, Richard K.,Houston, Timothy L.,Jackson, W. Roy
, p. 573 - 576 (2007/10/02)
One equivalent of HMPA induces 1,4-addition of the title anions predominantly through the α-position to cyclopentenone in THF at -78 deg C.In THF alone irreversible addition takes place to give mixtures comprising largely α- and γ-1,2 products.
