Tetrahedron p. 515 - 530 (1992)
Update date:2022-09-26
Topics:
Binns, Falmai
Hayes, Roy
Ingham, Stephen
Saengchantara, Suthiweth T.
Turner, Ralph W.
et al
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 deg 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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