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Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains
Author(s) -
Dobis Silvia,
Schollmeyer Dieter,
Gao Chunmei,
Cao Derong,
Meier Herbert
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700140
Subject(s) - chemistry , conformational isomerism , regioselectivity , alkane stereochemistry , stereochemistry , crystallography , photochemistry , crystal structure , organic chemistry , molecule , catalysis
Irradiation of 9‐(arylmethoxymethyl)anthracenes 3 leads either to a cyclomer and cyclodimer mixture ( 3a → 4a , 5a ), to selectively formed dimers ( 3b → 5b ), or a selectively formed cyclomer ( 3c → 4c ). The [4π+4π]cyclodimerization is under the conditions used a regioselective head‐to‐tail process. In the crystals of the dimers 5a , b , the sidechains are attached in an antiperiplanar position related to the CC bonds generated in the dimerization. In solutions, however, the structures consist of three rotamers the equilibration of which was studied by temperature‐dependent NMR spectra. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)