Premium
Organic phosphorus compounds 53 preparation and properties of bis‐(chloromethyl)‐phosphinic and ‐thiophosphinic acid derivatives as well as tertiary phosphine oxides and sulfides containing two ClCH 2 groups [1]
Author(s) -
Maier Ludwig
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540617
Subject(s) - chemistry , phosphine , chloride , medicinal chemistry , yield (engineering) , reagent , organic chemistry , phosphorus trichloride , derivative (finance) , phosphorus , catalysis , materials science , economics , financial economics , metallurgy
Bis‐chloromethyl‐phosphinates, ‐thiophophinates, and ‐phosphinic amides are formed in fair yield by treating either bis‐chloromethyl‐phosphinic or‐thiophosphinic chloride with alcohols, thiols, or amines in the presence of equivalent amounts of acid binding agents. Unexpectedly, the thiophosphinates show no insecticidal activity and only the β‐cumaryl derivative exhibits a low herbicidal activity. Reduction of bis‐chloromethyl‐thiophosphinic chloride to bis‐chloromethyl‐phosphinous chloride is effected with (PhO) 3 P at 170°. Interaction of this chloride, (ClCH 2)2 PCl, with Grignard reagents yields tertiary phosphines, which at slightly above room temperature are unstable, but which may be characterized as oxides or sulfides.