Hydrocarbons, hydrocarbon tosylhydrazones, synthesi

Synthesis and subsequent thermal decomposition of aryldiazomethanes under standard Bam-ford-Stevens conditions has also been utilized to prepare aryl-substituted cyclopropanes. When benzaldehyde tosylhydrazone is mixed with solid sodium methoxide in naphthalene, phenan-threne, and anthracene and heated above 130°C, phenylcarbene is generated. All the three aromatic hydrocarbons are attacked at the site of highest double-bond character to give, albeit in low yield, norcaradienes. The best results were obtained with naphthalene, which gave 1-phenyl-la,7b-dihydro-l//-cyclopropa[a]naphthalene (7) in 9% yield. ... 

Shapiro-Heath olefin synthesis (2, 418-419 4, 511 5, 678-679 6, 598-599). Vedejs has mentioned that LDA can be used instead of alkyllithiums for conversion of the more typical tosylhydrazones into olefins at 0" in THF. This variation was used in the synthesis of a new (CH)i2-hydrocarbon (1). 

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