Tetrahedron Letters p. 5411 - 5414 (1987)
Update date:2022-07-30
Topics:
Wiberg, Kenneth B.
McClusky, John V.
The reaction of 1,1-dibromo-2,3-bis(chloromethyl)cyclopropane with methyllithium leads initially to ring closure to 1-bromo-2-chloromethylbicyclo<1.1.0>butane.Further reaction leads to an unstable compound which reacts with phenylthiol to give 2-vinyl-1-cyclopropyl phenyl sulfide and undergoes thermal rearrangement at <*> -50 deg C to give cyclopentadiene.Strong evidence is presented which suggests that tricyclo<2.1.0.01,3>pentane may be the intermediate.
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