102299-06-9Relevant academic research and scientific papers
THERMAL ELECTROCYCLIC RING-OPENING OF CYCLOBUTENES: STEREOSELECTIVE ROUTES TO FUNCTIONALISED CONJUGATED (Z,E)- AND (E,E)-2,4-DIENALS
Binns, Falmai,Hayes, Roy,Ingham, Stephen,Saengchantara, Suthiweth T.,Turner, Ralph W.,et al
, p. 515 - 530 (2007/10/02)
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.
Thermal electrorocyclic ring-opening of cyclobutenes: Substituents with complementary conrotatory preferences induce high stereoselectivity
Hayes, Roy,Ingham, Stephen,Saengchantara, Suthiweth T.,Wallace, Timothy W.
, p. 2953 - 2954 (2007/10/02)
The thermal transformation of cis-disubstituted cyclobutenes into conjugated (Z,E)-dienes is stereoselective when the electronic and, to a lesser degree, steric effects of the substituents induce complementary conrotatory preferences at the reaction termini.
Stereoselective Routes to Functionalised Hexa-2,4-dienals from Cyclobutenes
Ingham, Stephen,Turner, Ralph W.,Wallace, Tomothy W.
, p. 1664 - 1666 (2007/10/02)
6-Substituted (2Z),(4E)- and (2E),(4E)-hexa-2,4-dienals have been prepared from a cyclobutene derivative via stereoselective electrocyclic ring-opening and isomerisation processes.
