REACTIVITY OF CYCLOPENTENYL-ANION ANALOGOUS HETEROCYCLES: SYNTHESIS AND 1,5-ELECTROCYCLISATION OF HOMOPHOSPHOLE

Article abstract of DOI:10.1016/S0040-4039(00)99430-9

The key step of a novel homophosphole synthesis is the reaction of the phospholes 3 with diazomethane in the presence of water leading surprisingly to the oxidized 1,3-dipolar cycloadducts 7.The 1,5-electrocyclization of homophosphole was observed by the racemization of optically active 10c at 120 deg C to be 641 times slower than of homofuran 1a.The activation barrier seems to be largely determined by the barrier of invension at the phosphorus which has to proceed concomitantly.