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New light on the mechanism of the solid state [2+2] cycloaddition of alkenes: a database analysis


Reference:

Allen, F. H., Mahon, M. F., Raithby, P. R., Shields, G. P. and Sparkes, H. A., 2005. New light on the mechanism of the solid state [2+2] cycloaddition of alkenes: a database analysis. New Journal of Chemistry, 29 (1), pp. 182-187.

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Abstract

The mechanism of the solid state [2 + 2] cycloaddition of alkenes has been investigated using the structure correlation method based on geometrical data calculated from single crystal X-ray diffraction studies retrieved from the Cambridge Structural Database (CSD). Searches were carried out for non-bonded alkene...alkene reactant interactions, within a limiting C...C separation of the sum of van der Waals radii plus 20%, and for bonded cyclobutane product fragments. The results were visualised and interpreted using principal component analysis and symmetry deformation coordinates. The reaction pathway for [2 + 2] cycloaddition was established and it was shown that ( a) the alkene moieties are not required to be parallel for the reaction to occur and (b) a large twist angle of the reacting alkene fragments is permissible to form a puckered cyclobutane reaction product, as long as similar intra-annular valence angles are maintained around the four-membered ring.

Details

Item Type Articles
CreatorsAllen, F. H., Mahon, M. F., Raithby, P. R., Shields, G. P. and Sparkes, H. A.
DOI10.1039/b412989j
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code4849
Additional InformationID number: ISI:000226164900023

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