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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Bibliographic Details
Published inHeterocycles Vol. 87; no. 6; pp. 1319 - 1326
Main Authors Akita, Motoko, Mohri, Sin-ya, Takahashi, Mai, Kobayashi, Keiji
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHOTOCYCLOADDITION
CRYSTAL-STRUCTURES
SWITCHES
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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.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-13-12718