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The spiro-bicyclic ylide(4) has been synthesized from 1-methyl - phosphorinane (5) via a phosphonium salt precursor [(CH 2 ) 5 P⊕(CH 3 )-(CH 2 ) 4 Br⊖Bre (6) which is cyclized with KH. Two other isomeric ylides (4 a , b) are detected in the reaction mixture by NMR spectroscopy. 4 is characterized by IR, MS,  1 H,  13 C and  31 P NMR spectroscopy, and through conversion into the corresponding phosphonium cation [(CH 2 ) 5 P(CH 2 ) 5 ] +  (7). A lithiated derivative (8) is obtained in the metalation reaction with LiCH 3 .

zeitschrift für naturforschung b

Ein spiro-bicyclisehes Phosphor-ylid und sein korrespondierendes Phosphoniumkation / A Spiro-bicyclic Phosphorus Yhde and its Corresponding Phosphonium Cation