
TY  - JOUR
A1  - Brown, RFC 
A1  - Coulston, KJ 
A1  - Eastwood, FW 
A1  - Vogel, C 
T1  - Scrambling of the Label in [<sup>13</sup>C<sub>2</sub>] Biphenylene Obtained on Pyrolysis of [1,6,<sup>13</sup>C<sub>2</sub>] and [2,3,<sup>13</sup>C<sub>2</sub>]-2-(3',3'-Dimethyltriazenyl)\benzoic Acid
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1988
VL  - 41
IS  - 11
SP  - 1687
EP  - 1695
KW  - 
UR  - https://doi.org/10.1071/CH9881687 
N2  - Flash vacuum pyrolysis of 2-(3&#8242;,3&#8242;-dimethyltriazenyl)benzoic acid (6) above 350&3176; gives biphenylene and N,N- dimethylaniline. The acid (6) was synthesized with 13C2 labels placed as in (13) to generate [1,6- 13C2] benzyne. F.v.p . of labelled acid (13) from 400-850&#176; gave biphenylene samples which showed 13C spectra consistent with an increasing extent of carbon rearrangement from [1,6-13C2] benzyne to [1,3-13C2] benzyne with increasing temperature. This is in accord with direct rearrangement of benzyne (Scheme 1) but it is probable that more than one mechanism is operating. The labelling evidence suggests that N,N- dimethylaniline is formed by re-addition of dimethylamine to benzyne. 
ER  -

