Title of article
Three types of products by carbon nucleophiles toward methoxyphenylacetylenic sulfones
Author/Authors
Chia-Yi Cheng، نويسنده , , Minoru Isobe and Kunio Miki، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
9
From page
9957
To page
9965
Abstract
Methoxy-arylacetylenic sulfones were examined to react with various carbanion nucleophiles to result in the three types of products; thus, (i) nucleophiles (MeLi·LiBr, Vinyl MgBr, LiCH2CN) showed the α-addition, however, (ii) Li–Ctriple bond; length of mdashC–TMS afforded β-addition (conjugate addition) products. The (iii) displacement reaction through α-addition/isomerization/trans-elimination was enhanced by the presence of ortho-methoxy group at high temperature. The heteroatom nucleophiles (nitrogen, oxygen or sulfur atom) in a protic solvent provided only conjugate addition products as reported.
Keywords
?-Addition , Displacement , Conjugate addition , Chelation effect , Isomerization , trans-Elimination , Acetylenic sulfone , ?-Addition
Journal title
Tetrahedron
Serial Year
2011
Journal title
Tetrahedron
Record number
1103971
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