Carbene-Carbene Rearrangements: Evidence for a Cyclopropene Intermediate

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Solvent was removed. No trace of adduct 4_4 was indicated by nmr or tic (benzene) of the residue.
106 Low Temperature Photolysis of the Sodium Salt oi: 5/7- Dibenzo [a, clcyclohepten-5-one Tosylhydrazone (41^') in the Presence of Diethylamine .--a) 5//-Dibenzo [a, c] cyclohepten- 5-one tosylhydrazone sodium salt (41^') (0.20 g, 0.50 mniol) and diethylamine (2.50 g, 34. mmol , distilled from LAII) were mixed in 20 ml dry tetrahydrofuran. The solution was photol- yzed 45 minutes at -60°. The reac
...tion mixture was warmed to room temperature, and the sodium toluenesulf inate dihydrate^^ (0.074 g, 0.35 mmol, 69% yield) was filtered off.
Solvents were removed, and the H-nmr spectrum of the residue gave no indication of the presence of a diethylamine addi- tion product (no ethyl signal) . Both nmr and tic of the product mixture were similar to those of reaction mixtures from photolysis of £1' in the absence of trapping reagents or in the presence of ineffective traps such as styrene or dimethyl f umarate .


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