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Direct Formation of a Substituted [5.5.5.5]Fenestrane by Intramolecular Arene‐Olefin Photocycloaddition
Author(s) -
Mani Jürg,
Schüttel Stefan,
Zhang Cong,
Bigler Peter,
Müller Christian,
Keese Reinhart
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720311
Subject(s) - chemistry , intramolecular force , olefin fiber , cycloaddition , derivative (finance) , stereochemistry , medicinal chemistry , intramolecular reaction , organic chemistry , catalysis , financial economics , economics
In a search for further synthetic routes to substituted [5.5.5.5] fenestranes, compound 1a , a derivative of 7‐methoxyindane, was photolyzed. Two of the three photoproducts, viz. the [3.5.5.5]fenestrane 3a and the isomer 4a , are formed according to the expected intramolecular meta ‐cycloaddition. A different mechanism is suggested for the formation of the major component 2a .