Tetrahedron p. 2717 - 2726 (1985)
Update date:2022-08-05
Topics:
Cristau
Plenat
Duc
Bennamara
A new way to 1,4 butadienylene bisphosphonium salts 2 is given, using a base-catalyzed double isomerization process on acetylenic precursors 3. The precursor can be synthetized by nucleophilic substitution of 1,4-diiodo 2-butyne with triphenylphosphine. The selection of the 1,4-dihalo 2-butyne has a strong influence on the course of the reaction which, besides that, can lead to exclusive formation of a new stabilized ylid-disalt 5. The stereoselectivity of the t.butylamine induced double isomerization allows the isolation of the kinetic product, the (Z, E) 1,4-butadienylene bisphosphoniun salt, which is then readily converted into the more stable (E, E) isomer.
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