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Through-bond interactions in the diradical intermediates formed in the rearrangements of bicyclo(n.m.0)alkatetraenes

The intermediates and transition structures in the degenerate thermal rearrangements of bicyclo[4.4.0]deca-2,4,7,9-tetraene (1c), bicyclo[5.5.0]dodeca-2,4,8,10-tetraene (11b), and bicyclo[5.4.0]undeca-2,4,8,10-tetraene (14) have been located by (U)B3LYP/6-31G(d) calculations. The singlet−triplet ene...

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Main Authors: Lovitt, Charity Flener (Author) , Dong, Hao (Author) , Hrovat, David A. (Author) , Gleiter, Rolf (Author) , Borden, Weston Thatcher (Author)
Format: Article (Journal)
Language:English
Published: 09/24/2010
In: Journal of the American Chemical Society
Year: 2010, Volume: 132, Issue: 41, Pages: 14617-14624
ISSN:1520-5126
DOI:10.1021/ja106329t
Online Access:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1021/ja106329t
Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/ja106329t
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Author Notes:Charity Flener Lovitt, Hao Dong, David A. Hrovat, Rolf Gleiter, and Weston Thatcher Borden

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520 |a The intermediates and transition structures in the degenerate thermal rearrangements of bicyclo[4.4.0]deca-2,4,7,9-tetraene (1c), bicyclo[5.5.0]dodeca-2,4,8,10-tetraene (11b), and bicyclo[5.4.0]undeca-2,4,8,10-tetraene (14) have been located by (U)B3LYP/6-31G(d) calculations. The singlet−triplet energy differences (ΔEST) in the diradical intermediates (tricyclo[4.4.0.02,7]deca-3,8-dien-5,10-diyl (2c), tricyclo[5.5.0.05,11]dodeca-2,8-dien-4,10-diyl (12b), and tricyclo[5.4.0.05,11]undeca-2,8-dien-4,10-diyl (15)) have been computed, using both UB3LYP and (6/6)CASPT2 calculations. ΔEST in 2c, in which a four-membered ring is anti-bridged by two allylic radicals, is computed to be larger by a factor of 5 than ΔEST in 15, in which the anti-bridged ring is five-membered, and by a factor of 10 than that in 12b, in which the anti-bridged ring is six-membered. The reasons for the much larger interaction between two allylic radicals through the bonds of the four-membered ring in 2c than through the bonds of the five-membered ring in 15 or the six-membered ring in 12b are discussed, and the consequences of the large, through-bond stabilization of the singlet state of 2c are described. 
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