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The preparation and absolute configuration of some chiral O,S-dialkyl phosphoramidothioates

โœ Scribed by C.Richard Hall; Thomas D. Inch

Book ID
104235645
Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
224 KB
Volume
18
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Phosphoramidothioates are of biological interest because of their insecticidal properties.' Chemically, such compounds merit detailed study because the P-O, P-S and P-N bonds may all be broken under mild conditions, the preponderant reaction depending critically on the reaction conditions employed.

2 To facilitate studies attempting to relate chemical and biological properties of phosphoramidothioates a series of chiral O,S-dialkyl phosphoramidothioates was required.

3 In this paper are described the preparations of such compounds by a stereospecific route which allows assignment of their absolute configurations.

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Ca. 18000 US%/kg of absolute oil. We are indebted to Prof. J. Garner0 and D . Joulain for a copy of this analysis. This is an energetically unfavorable (uphill) transformation. Indeed, 13c is totally converted into 16c under basic conditions (MeONa, MeOH, 0.1 mol-equiv., 2 5 O ; 90%). For a comparis