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Synthesis of 3‐Trifluoro‐2‐hydroxy/amino‐1‐fluoropropylphosphonates †
Author(s) -
Zheng WeiHong,
Yuan ChengYe
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690219
Subject(s) - chemistry , hydrogenolysis , hydrolysis , amine gas treating , catalysis , medicinal chemistry , reaction mechanism , aqueous solution , proton , reaction conditions , organic chemistry , physics , quantum mechanics
Reaction of diethyl 2,2‐difluoro‐3‐( α ‐methylbenzyl)imino‐4,4,4‐trifluoropropanephosphonate ( 3 ) with triethyl‐ amine afforded a mixture of normal [1,3]‐proton shift reaction product 5 and its HF‐eliminated compound 6 Z in 1:1 ratio. Upon hydrolysis, this reaction mixture gave solely 1,3,3,3‐tetrafluoro‐2‐dioxypropanephosphonate ( 9 ). Reaction of 3 with DBU provided only 6 , in which the ratio of E / Z forms was dependent on the reaction conditions. Aqueous hydrolysis of 6 led to 9 . Catalytic hydrogenation and hydrogenolysis of 6 gave geometric isomers of 11 as expected. The reaction mechanism involved was discussed.