Decomposition of benzenediazonium-3-carboxylate: transient 1,3-dehydrobenzene

✍ Scribed by R.Stephen Berry; John Clardy; Margaret E. Schafer

• Book ID: 104249996
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 314 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99516-4

✦ Synopsis

We wish to report the evidence for a transient C6H1( species which, from existing information, appears to be 1,3dehydrobenzene.

This substance, identified principally by its mass spectrum, has a lifetime in the gas phase comparable to that of benzyne, the 1,2_dehydrobenzene.

The method of production and identification of the supposed 1,x-isomer follows that used for the long-lived 1,4-isomer1 and the transient 1,2-isomer. 2y3 Flash-initiated decomposition of an unstable precursor, in khis case benzenediazonium-3-carboxylate, ** generates N2, CO2 and organic products. We have studied the process and the products by following both the mass spectrum and the optical spectrum as functions of time.

In order to present the evidence for the transient C6Hq and for the assignment of its structure as 1,3-dehydrobenzene, we shall discuss, first, the optical spectrum, and second, the mass spectrum. We then present the analysis of the latter from which the structure is inferred.

OPTICAL SPECTRUM: Optical spectra of the gaseous decomposition products provide some information, albeit less than one might hope. As with ortho and para isomers, there 1011