INTRAMOLECULAR [2 pi+2 pi]-PHOTOCYCLIZATION AND CONFORMATIONAL PREFERENCE OF 5-(2-BENZO[b]THIENYL)-5-ETHOXY-5H-DIBENZO[a,d]CYCLOHEPTENE
The photoirradiation of 5-(2-benzo[b]thienyl)-5-ethoxy-5H-dibenzo-[a,d]cycloheptene (2) in acetonitrile afforded a cagelike tetracyclic compound (1) via intramolecular [2 pi+2 pi]-photocycloaddition. The molecular and crystal structures of 1 and 2 were characterized by a single-crystal X-ray diffrac...
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Published in | Heterocycles Vol. 87; no. 6; pp. 1319 - 1326 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier
2013
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Subjects | |
Online Access | Get more information |
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Summary: | The photoirradiation of 5-(2-benzo[b]thienyl)-5-ethoxy-5H-dibenzo-[a,d]cycloheptene (2) in acetonitrile afforded a cagelike tetracyclic compound (1) via intramolecular [2 pi+2 pi]-photocycloaddition. The molecular and crystal structures of 1 and 2 were characterized by a single-crystal X-ray diffraction study. The formation of the cycloadduct is discussed in relation to the preferable conformation of the central C-C bond in 2, which was revealed to be in restricted rotation on the basis of the temperature-dependent H-1 NMR spectra. |
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ISSN: | 0385-5414 1881-0942 |
DOI: | 10.3987/COM-13-12718 |