Three types of products by carbon nucleophiles toward methoxyphenylacetylenic sulfones |
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| Authors: | Chia-Yi ChengMinoru Isobe |
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| Affiliation: | Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan |
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| 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-C C-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. |
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| Keywords: | Acetylenic sulfone α-Addition β-Addition Displacement Conjugate addition Chelation effect Isomerization trans-Elimination |
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