Journal of Organic Chemistry p. 348 - 352 (1992)
Update date:2022-08-03
Topics:
Udayakumar, B. S.
Schuster, Gary B.
The photochemistry of 2,2"-ethano-bridged m-terphenyl derivatives 4, 8, and 9 was investigated.These compounds are chiral and may be suitable photoresolvable additives to discotic liquid crystals.Unlike their unbridged analogues, 4, 8, and 9 rearrange rapidly when irradiated with UV light to the o-terphenyl compounds 10,11, and 12, respectively.This rearrangement is likely to proceed through an intermediate benzvalene valence-bond isomer.The high reactivity of the 2,2"-ethano-bridged compounds is attributed to distortion in their lowest excited singlet states and to the relief of strain when the ortho isomers are formed.
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