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The serendipitous synthesis of an oxabicyclo [3.2.0] heptadiene

✍ Scribed by M.J. Goldstein; M.W. Johnson; R.T. Taylor

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 213 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87607-8

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✦ Synopsis

Ah&m&: 5,6-Dlhaloblcyclo[2.l.l]hexanes resist simple nucleophlllc displacement In several ways. Least expected of these is the 2+1 rearrangement The energy needed to assemble Z-oxablcyclo[3.2.O]heptadlenes 1s normally supplied by photons.

1 An alternatzve source, the strain energy of a precursor, was once used to prepare the hexamethyl derivative, but only lnefflclently (16%) and at a high temperature (190") 2 We now report a novel rearrangement that enables precursor strain to provide the 3-cyano derivative (1) 3

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