Journal of Organic Chemistry p. 3001 - 3002 (1990)
Update date:2022-08-04
Topics:
Mathur, Naresh C.
Shechter, Harold
5-Diazo-3-methyluracil reacts with varied benzenes to yield 3-methyl-5-aryluracils by apparent singlet carbene addition and homolytic rearrangement of spironorcaradiene intermediates. 5-Diazouracil, however, thermolyzes with rearrangement and loss of nitrogen to form (2,5-dioxo-3-imidazolin-4-yl)methylene, which reacts with benzene and cyclooctane to give 5-cycloheptatrienylidene-2,4-imidazolidinedione and (E)- and (Z)-5-(cyclooctylmethylene)-2,4-imidazolidinediones, respectively.
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