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A new mechanism for nucleophilic substitution at a thiophosphoryl centre revealed by the reaction of diisopropylamine with PSCl3.

Chemical communications (Cambridge, England) (2005-06-02)
Martin J P Harger
ABSTRACT

The reaction of PSCl3 with Pr(i)2NH at 60 degrees C affords the disubstitution product (Pr(i)2N)2P(S)Cl without first forming the monosubstitution product Pr(i)2NP(S)Cl2; a P(III) compound (possibly PCl3) generated in situ seems to be a crucial intermediate.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Lithium diisopropylamide solution, 2.0 M in THF/heptane/ethylbenzene
Sigma-Aldrich
Diisopropylamine, ≥99.5%
Sigma-Aldrich
Lithium diisopropylamide, 97%
Sigma-Aldrich
Diisopropylamine, purified by redistillation, 99.95%
Sigma-Aldrich
Thiophosphoryl chloride, 98%
Sigma-Aldrich
Diisopropylamine, puriss. p.a., ≥99.0% (GC)
Supelco
Diisopropylamine, analytical standard
Sigma-Aldrich
Lithium diisopropylamide, 10 wt. % suspension in hexanes