Studies on Phosphonium Ylides, XXIV: Reactions of Phosphorus Ylides with 1,2,3,4-Tetrahydro1-Naphthylidene-Malononitrile

1,2,3,4-tetrahydro-1-naphthylidene-malononitrile (1) reacts with carbethoxymethylene and carbmethoxymethylene- triphenylphosphoranes (2a, 2b) to give the new phospho-ranylidenecyclopentaylidene products (4a, 4b, and 5), respectively. The treatment of (1) with phosphorus ylide 2c afforded the new phosphonium ylide 6. Moreover, the application of reagent (2d) on (1) renders compound 7. On the other hand, when N-phenyliminotriphenylphosphorane (3) reacts with (1), the corresponding adduct (8) was obtained together with triphenylphosphine. Mechanisms accounting for the formation of new products are discussed, and probable structures of products are presented based on analytical and spectroscopic data.

Keywords:

• Cyclopentaylidene-naphthalen-1-ylidene-acetamide
• naphthylidene-malononitrile
• phosphonium ylides