Methyleneketenes and methylenecarbenes. XII. Thermal rearrangement of acetylene

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Abstract
Flash vacuum pyrolysis of 1,2,3,4-tetrafluoro-9-methoxy-9,10-dihydro- 9,10-ethenoanthracene[12-13C;10,12-D2], (600°) gives doubly labelled acetylene HC≡13CD. At temperatures of 700° and greater, the ethenoanthracene gives a mixture of HC≡13CD and DC≡13CH. Formation of the acetylene at 600° followed by pyrolysis at 850° confirmed that it is the free acetylene that undergoes intramolecular rearrangement: ����������������������������������� >700.����������������������������� HC≡13CD ↔ DC≡13CH The pattern of labelling in the acetylene was determined by allowing it to react with bromine and examining the resulting 1,1,2,2- tetrabromoethane by p.m.r. and infrared spectroscopy. Mass spectral studies on the tetrabromoethane showed that no significant intermolecular hydrogen exchange takes place up to 1050°.

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