
%0 Journal Article
%A Brown, RFC 
%A Eastwood, FW 
%A Jackman, GP 
%T Methyleneketenes and methylenecarbenes. XII. Thermal rearrangement of acetylene
%J Australian Journal of Chemistry
%D 1978/03/01
%V 31
%N 3
%P 579-586
%K 
%R https://doi.org/10.1071/CH9780579
%U https://www.publish.csiro.au/paper/CH9780579 
%X Flash vacuum pyrolysis of 1,2,3,4-tetrafluoro-9-methoxy-9,10-dihydro- 9,10-ethenoanthracene[12-13C;10,12-D2], (600&#176;) gives doubly labelled acetylene HC&#8801;13CD. At temperatures of 700&#176; and greater, the ethenoanthracene gives a mixture of HC&#8801;13CD and DC&#8801;13CH. Formation of the acetylene at 600&#176; followed by pyrolysis at 850&#176; confirmed that it is the free acetylene that undergoes intramolecular rearrangement:                                     >700.                              HC&#8801;13CD &#8596; DC&#8801;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&#176;. 
