@article{5a783d2c5b5840dbb5a2fa84875d72cc,
title = "Synthesis and ring-opening metathesis of tetraalkoxy-substituted [2.2]paracyclophane-1,9-dienes",
abstract = "Tetraalkoxy-substituted [2.2]paracyclophane-1,9-dienes can be prepared in three steps from dithia- ACHTUNGTRENUNG[3.3]paracyclophanes. A mixture of pseudo-geminal and pseudo-ortho diastereomers is produced and the pure compounds can be separated by fractional crystallization. The solid state structures of these diastereomers reveal strongly distorted aromatic rings consistent with high levels of ring strain. Reaction of these diastereomers with the second generation Grubbs catalyst shows that only the pseudo-geminal isomer can be ring opened to give cis,trans-distrylbenzenes. The origin of this selectivity is discussed and the photoisomerization of the as-formed cis,- trans-product to the all trans isomer is demonstrated. Copyright {\textcopyright} 2011 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",
keywords = "cyclophanedienes, isomers, metathesis, phenylenevinylenes, strained molecules",
author = "Yu, \{Chin Yang\} and Madeleine Helliwell and James Raftery and Turner, \{Michael L.\}",
note = "CAN 155:152226 25-29 Benzene, Its Derivatives, and Condensed Benzenoid Compounds School of Chemistry,The University of Manchester,Manchester,UK. Journal 1313496-52-4P Role: PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (crystal structure, failed ring-opening metathesis; prepn. and ring-opening metathesis of tetraalkoxy-substituted paracyclopanedienes); 1313496-49-9P; 1313496-51-3P; 1313496-87-5P Role: PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (crystal structure; prepn. and ring-opening metathesis of tetraalkoxy-substituted paracyclopanedienes); 246047-72-3 (Grubbs second generation catalyst) Role: CAT (Catalyst use), RCT (Reactant), USES (Uses), RACT (Reactant or reagent) (prepn. and ring-opening metathesis of tetraalkoxy-substituted paracyclopanedienes); 109-92-2 (Vinyl ethyl ether); 147274-72-4; 1313052-70-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. and ring-opening metathesis of tetraalkoxy-substituted paracyclopanedienes); 1313052-71-9P; 1313496-50-2P; 1313496-53-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and ring-opening metathesis of tetraalkoxy-substituted paracyclopanedienes); 1313052-72-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and ring-opening metathesis of tetraalkoxy-substituted paracyclopanedienes)",
year = "2011",
month = jun,
day = "14",
doi = "10.1002/chem.201003147",
language = "English",
volume = "17",
pages = "6991--6997",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "John Wiley \& Sons Ltd",
number = "25",
}