Concepedia

Complete retention of configuration in the nucleophilic substitution of 1-phenylbenzo[b]thiophenium salts by alkoxide anions

Tsugio Kitamura, Masa-Aki Miyaji, S. SODA, Hiroshi Taniguchi

Journal of the Chemical Society Chemical Communications · 1995 · 10 citations · 8 references

DOI

Concepts

Abstract

Reaction of 1,2,3-triarylbenzo[b]thiophenium salts with alkoxide anions results in the exclusive formation of (Z) alkoxy-substituted alkenes, indicating that the nucleophilic ring-opening reaction proceeds with complete retention of configuration.

References

8

Ligand-coupling reactions of hypervalent species

Shigeru Ōae, Yuzuru Uchida · Accounts of Chemical Research · 1991 · 179 citations

, , +6

The rapid steps in nucleophilic vinylic addition-elimination substitution. Recent developments

Zvi Rappoport · Accounts of Chemical Research · 1992 · 124 citations

, , +7

Inversion of configuration in nucleophilic vinylic substitutions of (E)-.beta.-alkylvinyliodonium tetrafluoroborates with halides

Masahito Ochiai, Kunio Oshima, Yukio Masaki · Journal of the American Chemical Society · 1991 · 107 citations

, , +10

An authentic case of in-plane nucleophilic vinylic substitution: the anionotropic rearrangement of di-tert-butylthiirenium ions into thietium ions

Vittorio Lucchini, Giorgio Modena, Lucia Pasquato · Journal of the American Chemical Society · 1993 · 45 citations

, , +7

Stereoselection in nucleophilic substitution at an sp2 carbon

Sidney I. Miller · Tetrahedron · 1977 · 42 citations

, , +8