224293-78-1Relevant articles and documents
Organophosphorus compounds; 129. Mesitylphosphaacetylene: Synthesis and reactivity studies of a new phosphaalkyne
Mack, Andreas,Pierron, Elke,Allspach, Thomas,Bergstra??er, Uwe,Regitz, Manfred
, p. 1305 - 1313 (1998)
Mesitylphosphaacetylene (1b) has been synthesized by AlCl3 initiated elimination of bis(trimethylsilyl) ether from the phosphaalkene 2b. This new phosphaalkyne undergoes [3+2] cycloaddition reactions with diazo compounds (→ 6a,b), azides (→ 8a-c), and nitrile oxides (→ 10a,b) to yield five-membered heterocyclic products. The mesoionic reaction partners 11 and 13 react with 1b under elimination of CO2 and COS, respectively, to furnish the 1,3-aza- and 1,3-thiaphospholes 12 and 14. Reaction of 1b with buta-1,3-diene leads to the diphosphatricyclooctene 18; it has been shown that the 1-phosphacyclohexa-1,4-diene 15 (characterized by an X-ray structure analysis of its W(CO)5 complex 17) is an intermediate in the multistep reaction. Moreover, 1b has been characterized by Diels-Alder reactions with the cyclobutadiene 19 and the azacyclobutadiene 21 to afford the Dewar hetarenes 20 and 22.