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Issue 1, 2007
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Synthesis, stereochemistry, and photochemical and thermal behaviour of bis-tert-butyl substituted overcrowded alkenes

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Abstract

In order to study the structural limits in the design of molecular motors, a tert-butyl substituted analogue was prepared. The unexpected photochemical and thermal isomerisation processes and the stereochemistry of new overcrowded alkene 5 are described. The bis tert-butyl substituted alkenes were synthesised in a five-step sequence with an overall yield of 7.5%. Structural assignments of the isomers based on experimental data were supported by calculations of all four isomers of the alkene. X-Ray crystal analysis showed a strongly twisted alkene (torsion angle 39°) for a less stable photochemically generated cis-isomer.

Graphical abstract: Synthesis, stereochemistry, and photochemical and thermal behaviour of bis-tert-butyl substituted overcrowded alkenes

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The article was received on 01 Aug 2006, accepted on 25 Oct 2006 and first published on 10 Nov 2006


Article type: Paper
DOI: 10.1039/B611070C
Citation: Org. Biomol. Chem., 2007,5, 87-96

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    Synthesis, stereochemistry, and photochemical and thermal behaviour of bis-tert-butyl substituted overcrowded alkenes

    M. K. J. ter Wiel, M. G. Kwit, A. Meetsma and B. L. Feringa, Org. Biomol. Chem., 2007, 5, 87
    DOI: 10.1039/B611070C

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