Treatment of 4‐chloro‐5‐methyl‐2‐phenyl‐[4‐14C]pyrimidine with potassium amide in liquid ammonia yields a 4(5)‐ethynyl‐2‐phenylimidazole, in which the ethynyl group is attached to the radioactive carbon atom. This result indicates that during ring contraction the bond between C5 and C6 of the pyrimidine ring is broken.
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Meeteren et al. (1969) studied this question.
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