Intramolecular Nucleophilic Substitution of ω-Haloalkylphosphine Derivatives.
J Org Chem
; 82(19): 10271-10296, 2017 10 06.
Article
em En
| MEDLINE
| ID: mdl-28857562
ABSTRACT
ω-Haloalkylphosphine derivatives undergo the intramolecular nucleophilic substitution reaction upon treatment with a strong base, yielding either cycloalkylphosphine derivatives or heterocyclic phosphine derivatives. The selectivity of the cyclization of (ω-haloalkyl)alkylarylphosphine derivatives depends strongly on the distance between the electrophilic and nucleophilic carbon atoms and the structure of the phosphorus moiety. The desymmetrization of dimethylphenylphosphine sulfide followed by haloalkylation and cyclization led to the enantiomerically enriched tertiary phosphine sulfide, possessing a cyclohexyl fragment at the phosphorus.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2017
Tipo de documento:
Article