All articles of this category The reaction of tris[trimethylsilyl]phosphine ( 4a ) as well as of the lithium bis[trimethylsilyl]phosphide·; tetrahydrofuran complex ( 4b ) with 1-adamantoyl chloride ( 5 ) results in the formation of the phosphaalkene 7 in 67% or 96% yield, respectively. Subsequent sodium hydroxide or tetra- n -butylammonium fluoride-catalysed elimination of hexamethyldisiloxane from 7 at 20/90 °C gives rise to the phosphaalkyne 8 in 83 or 71% yield. The phosphaalkyne 8 undergoes smooth [3 + 2]cycloaddition reactions with 1,3-dipoles such as the nitrile oxide 9 , the diazo compounds 12a-c , and the azide 15 to produce the phospholes 11 , 14a-c , and 16 , respectively. The phosphaalkene 7 reacts with the dipoles 9 and 12a to give the same cycloadducts 11 and 14a , respectively. In these two reactions, the primary adducts undergo spontaneous ( 10 → 11 ) or sodium hydroxide-catalysed ( 13 → 14a ) elimination of hexamethyldisiloxane.
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Allspach et al. (1986) studied this question.