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On the effect of tether composition on cis/trans selectivity in intramolecular Diels-Alder reactions

Paddon-Row, Michael; Longshaw, Alistair; Willis, Anthony; Sherburn, Michael


Intramolecular Diels-Alder (IMDA) transition structures (TSs) and energies have been computed at the B3LYP/6-31+G(d) and CBS-QB3 levels of theory for a series of 1,3,8-nonatrienes, H2C=CH-CH=CH-CH2X-Z-CH= CH2 [-X-Z-=-CH2-CH2(1); -O-C(=O)- (2); -CH 2-C(=O)-(3); -O-CH2- (4); -NH-C(=O)- (5); -S-C(=O)- (6); -O-C(=S)- (7); -NH-C(=S)- (8); -S-C(=S)- (9)]. For each system studied (1-9), cis- and trans-TS isomers, corresponding, respectively, to endo- and exo-positioning of the -C-X-Z- tether with...[Show more]

CollectionsANU Research Publications
Date published: 2009
Type: Journal article
Source: Chemistry - An Asian Journal
DOI: 10.1002/asia.200800352


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