By Wolfgang Kirmse (Auth.)

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The product composition showed a definite phase dependence. The change from gas to liquid and solid phase reduced the yields of ethylene and acetylene, with a concomitant increase of apparent methylene insertion products (241). Observations on the statistical nature of the formation of various hexanes from rc-pentane (242) were confirmed with propane. The ratio of η-butane to isobutane approached 3 : 1 in the liquid and solid phases (241). Indiscriminate reaction with carbon-hydrogen bonds is characteristic of methylene.

0]hexane, and methylenecyclopentane, 1 5 - 2 0 % of dicyclohexylazine (752, 754). I R examination of the reaction mixture immediately following partial photolysis showed the presence of diazocyclohexane. It is likely that the dicyclohexylazine is formed from the diazo compound. Photolysis of pentamethylenediazirine in acetic acid led to the formation of 39 % of cyclohexyl acetate (752, 755). Since the diazirine does not react with acetic acid in the dark, it is probable that cyclohexyl acetate arises from trapping of the intermediate diazocyclohexane.

C H 30 ) 2C : ^CH \ ^ Χ + 3 γ -CO—OCH 3 / • · CH 3 + C0 2 ' (63) C H 3C O - O C H 3 Pyrolysis of the cyclic ketal [58] affords an almost quantitative yield of tetrachlorodiphenyl, and 95 % of the ketal bridge is accounted for by the equimolar quantities of ethylene and C 0 2 evolved (190,192). A concerted pathway for the fragmentation of [58] is rendered unlikely, however, by the fact that [58] decomposes much more slowly than does [53a]. , [59] (191). 6 C1 Çl ÇH 3 C l ^ ^ C O - O - C H - C H - C l + ^ m : H 3C H C=C H CH, X Quadricyclanone ketals have been investigated as potential sources of dialkoxycarbenes.

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