Tetrahedron p. 3521 - 3536 (1986)
Update date:2022-08-05
Topics:
Labaudiniere, L.
Burgada, R.
The thermal evolution of aryloxy or enoxyvinylphosphoranes 1 is reported.It leads to spirophosphoranes 2.The yield as well as the reaction time decrease when the ?-deficient character of the aryloxy or enoxy system increases.With very electron withdrawing systems, the main reaction is analogous to the second step of the Arbuzov reaction and gives rise to the vinylphosphonate 6 and to the corresponding aromatic ether 7.When the carboxylate group the nearest to the phosphorus atom is replaced by a phenyl group or an hydrogen atom, no spirophosphorane 2 is obtained.The hydrolysis of compounds 2, under mild condition, leads to a new class of phosphonates 3 and 16.
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