Science of Synthesis

Hoffman, R. V.; Cesare, V., Science of Synthesis, (2005) 21, 605.

There have been several reported cases of [3+2]-cycloaddition reactions involving α-lactams, although yields are generally poor. The formation of a hydantoin ring has been reported when 1-tert-butyl-3,3-dimethylaziridinone is reacted with phenyl isocyanate to give a mixture of two isomers of imidazolidine-2,4-dione in 25% yield (‌Scheme 21‌).[‌60‌] The ratio of the two isomers is 7:3. When less stable α-lactams are generated in situ in the presence of an isocyanate at −50°C, only hydantoins arising from 1—3 cleavage are formed.

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References

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• 8.Meeeee-Meee, (8888) M 88e, 88.