Anchimerically assisted substitution of a sulfinyl function of α-sulfinylhydrazones by thiols

Bosch, Hubert; Pflieger, Philippe; Mioskowski, Charles; Salaün, Jean‐Pierre; Durst, Francis

doi:10.1016/s0040-4039(00)79690-0

Cited by 3 publications

(1 citation statement)

References 5 publications

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“…R-NO 2 [36,37], R-S(=O) 2 R [38,39], R-S(=O)R [40]) will usually undergo substitution only under neutral or acidic conditions, what limits the choice of suitable nucleophiles. Electrophiles with such leaving groups (e.g.…”

Section: Good and Poor Leaving Groupsmentioning

confidence: 99%

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

Dörwald

2004

Side Reactions in Organic Synthesis

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Nucleophilic substitutions at sp 3 -hybridized carbon are among the most useful synthetic transformations, and have been thoroughly investigated [1][2][3]. The success of these reactions depends mainly on the structures of the nucleophile and electrophile, their concentration, and on the solvent and reaction temperature chosen. The structure of the electrophile in nucleophilic substitutions is of critical importance, because many unwanted side reactions result from unexpected reactivity of the electrophile.In Scheme 4.1 the mechanisms of typical monomolecular (Sn1) and bimolecular (Sn2) nucleophilic substitutions at a neutral electrophile with an anionic nucleophile are sketched. Sn1 reactions usually occur when the electrophile is sterically

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Section: Good and Poor Leaving Groupsmentioning

confidence: 99%

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

Dörwald

2004

Side Reactions in Organic Synthesis

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ChemInform Abstract: Anchimerically Assisted Substitution of a Sulfinyl Function in α‐ Sulfinyl Hydrazones by Thiols.

et al. 1992

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1992 mercaptans, thioethers mercaptans, thioethers (acyclic compounds) P 0430 -134Anchimerically Assisted Substitution of a Sulfinyl Function in α-Sulfinyl Hydrazones by Thiols.-The α-sulfinyl carboxaldehyde dimethylhydrazones (III), obtained by lithiation of the hydrazones (I) followed by treatment with methyl p-tolylsulfinate (II), react with the thiols (IV) to give the sulfides (V). A mechanism involving an acid-catalyzed anchimerically assisted elimination-addition process is discussed. -(BOSCH, H.; PFLIEGER, P.; MIOSKOWSKI, C.; SALAUEN, J.-P.; DURST, F.; Tetrahedron Lett. 32 (1991) 20, 2237-2240 Univ. L. Pasteur, Lab. Chim. Bio-Org., Ass. CNRS, Fac. Pharm., 67401Strasbourg, Fr.; EN)

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Tetrachalcogenafulvalenes with Four Additional Heteroatoms

Yamada¹,

Sugimoto²

2004

TTF Chemistry

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Anchimerically assisted substitution of a sulfinyl function of α-sulfinylhydrazones by thiols

Cited by 3 publications

References 5 publications

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

ChemInform Abstract: Anchimerically Assisted Substitution of a Sulfinyl Function in α‐ Sulfinyl Hydrazones by Thiols.

Tetrachalcogenafulvalenes with Four Additional Heteroatoms

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