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23.12.4.1.4.1 Variation 1: Azafulvenones by Wolff Rearrangement and Other Routes

DOI: 10.1055/sos-SD-023-00394

Tidwell, T. T.Science of Synthesis, (200623470.

3-(Oxomethylene)-3H-pyrrole (371) has been prepared by low temperature photochemical Wolff rearrangement of the α-diazo ketone 370 in a matrix as identified by the IR absorption at 2146cm1 (Scheme 146),[‌290‌] while flash-vacuum pyrolytic dehydration of 1H-pyrrole-2-carboxylic acid (372) gives the isomeric 2-(oxomethylene)-2H-pyrrole (373), also identified by the IR absorption at 2146cm1, which is trapped in a matrix and forms the dimer 374 (Scheme 146).[‌291‌,‌292‌] Photolysis of the diazo compound 375 gives the carbene 376, which upon carbon monoxide addition in a matrix forms 4-(oxomethylene)-4H-imidazole (377), identified by the IR absorption at 2153cm1 (Scheme 146).[‌293‌]

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