65173-35-5Relevant academic research and scientific papers
Singlet vs Triplet Reactivity of Photogenerated α,n-Didehydrotoluenes
Pedroli, Chiara,Ravelli, Davide,Protti, Stefano,Albini, Angelo,Fagnoni, Maurizio
, p. 6592 - 6603 (2017/07/15)
The reactivity of α,n-didehydrotoluenes (DHTs) in protic media (organic/aqueous mixtures) was explored by means of a combined computational and experimental approach. These intermediates were generated via a photoinduced double elimination process occurring in (chlorobenzyl)trimethylsilanes and led to the formation of a varied products distribution, depending on the isomer tested. Irradiation of ortho- and para-derivatives resulted, respectively, in the formation of triplet α,2- and α,4-DHTs, whose diradical reactivity led to both radical and polar products. On the other hand, irradiation of the meta-precursor led to the singlet α,3-DHT isomer. The latter showed a marked preference for the formation of polar products and this was rationalized, as supported by computational evidence, via the involvement of a zwitterionic species arising through interaction of the nucleophilic solvent with the benzylic position of the DHT.
Studies on the thermal generation and reactivity of a class of (σ,π)-1,4-biradicals
Myers, Andrew G.,Dragovich, Peter S.,Kuo, Elaine Y.
, p. 9369 - 9386 (2007/10/02)
(Z)-1,2,4-Heptatrien-6-yne and compounds that contain the (Z)-allene-ene-yne functional group or that form it in a serial reaction sequence were prepared and shown to undergo a mild thermal reaction to form aromatic products. All observations suggest that
