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Thermal electrocyclic ring opening of cyclobutenes stereoselective routes to functionalised conjugated z e and e e 2 4 dienals

Thermal electrocyclic ring opening of cyclobutenes stereoselective routes to functionalised conjugated z e and e e 2 4 dienals

Tetrahedron 48(3): 515-530

The cyclobutenecarbaldehyde 12 undergoes thermal electrocyclic ring-opening at low temperature, producing the (2Z,4E)-hexadienal 13 exclusively. By contrast, unsymmetrical derivatives of cis-3-cyclobutene-1,2-dicarboxylic acid undergo ring-opening at 80-110.degree. C with low levels of stereoselectivity, which vary according to the balance of the electronic and, to a lesser extent, the steric nature of the substituents located on the rehybridising carbon atoms.

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Accession: 007947265

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DOI: 10.1016/s0040-4020(01)89013-x

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