Tetrahedron p. 2441 - 2450 (1985)
Update date:2022-08-05
Topics:
Chmielewski, Marek
Kakuza, Zbigniew
Bekzecki, Czeslaw
Sakanski, Piotr
Jurczak, Janusz
Adamowicz, Halina
High-pressure (2+2)cycloaddition of toluene-4-sulphonyl isocyanate to glycals is examined.Reactions proceed regiospecifically to afford single products in case of all 3-substituted glycals.Upon heating or even after standing at room temperature adducts undergo retro-addition to give starting glycals.Various aspects of the cycloaddition are discussed, especially retro-reaction and rearrangement of β-lactams to α,β-unsaturated amides.
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