HIGH-PRESSURE (2+2)CYCLOADDITION OF TOLUENE-4-SULPHONYL ISOCYANATE TO GLYCALS

DOI: 10.1016/S0040-4020(01)96639-6

Source and publish data:

Tetrahedron p. 2441 - 2450 (1985)

Update date:2022-08-05

Topics:

Authors:

Chmielewski, Marek

Kakuza, Zbigniew

Bekzecki, Czeslaw

Sakanski, Piotr

Jurczak, Janusz

Adamowicz, Halina

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Article abstract of DOI:10.1016/S0040-4020(01)96639-6

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.

Full text of DOI:10.1016/S0040-4020(01)96639-6

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