Photocatalysis. 6. On the mechanism of the cyclotrimerization of trans-cycloheptene, catalyzed by copper(I) triflate
article
The trans-cycloheptene ligand in the copper(I) triflate-trans-cycloheptene complex cyclotrimerizes at 60??C in the presence of cis-cycloheptene. With use of cycloheptene-d4 or trans-cyclooctene it was established that cyclotrimerization is a process involving trans-cycloheptene molecules only. No cis-cycloheptene or trans-cyclooctene molecules are incorporated into the trimer. However, cis-cycloheptene exerts an accelerating effect on this reaction by replacing the reacted trans-cycloheptene at copper(I). The most likely explanation of these results is a concerted "template" cyclotrimerization process of either three (R)- or three (S)-trans-cycloheptene molecules around copper. Another possibility would be a two-step mechanism, involving a cupracyclopentane intermediate, irreversibly formed from two trans-cycloheptene molecules. No evidence for such an intermediate has been found so far. ?? 1981 American Chemical Society.
TNO Identifier
229119
ISSN
0002-7863
Source
Journal of the American Chemical Society, 103(23), pp. 6901-6904.
Pages
6901-6904
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