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Synthesis and Photochemistry of β,β′‐Di(2‐furyl)‐Substituted o ‐Divinylbenzenes: Intra‐ and/or Intermolecular Cycloaddition as an Effect of Annelation
Author(s) -
Škorić Irena,
Basarić Nikola,
Marinić Željko,
Višnjevac Aleksandar,
KojićProdić Biserka,
ŠindlerKulyk Marija
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200401005
Subject(s) - furan , cycloaddition , intramolecular force , intermolecular force , chemistry , bicyclic molecule , annulation , derivative (finance) , cyclophane , medicinal chemistry , intramolecular reaction , photochemistry , stereochemistry , crystal structure , molecule , organic chemistry , catalysis , financial economics , economics
New heteroaryl‐substituted o ‐divinylbenzenes, 2,2′‐(1,2‐phenylenedivinylene)difuran ( 9 ), 2,2′‐(1,2‐phenylenedivinylene)bisbenzo[ b ]furan ( 10 ), and 2,2′‐(1,2‐phenylenedivinylene)bisnaphtho[2,1‐ b ]furan ( 11 ), were prepared and irradiated at various concentrations; intramolecular photocycloaddition and intermolecular [2+2] twofold photoaddition reactions took place to give bicyclo[3.2.1]octadiene derivatives 12 – 14 and cyclophane derivatives 15 – 17 , respectively. Compound 11 was the most selective of these o ‐divinylbenzenes, which, owing to π–π intra‐ or intermolecular complexation, gave only the exo ‐bicyclo[3.2.1]octadiene derivative 14 at low concentrations, and only the cyclophane derivative 17 at high concentrations.