5412-39-5Relevant academic research and scientific papers
Arene 1,4-Diradical Formation from o-Dialkynylarenes
Semmelhack, M. F.,Neu, Thomas,Foubelo, Francisco
, p. 5038 - 5047 (2007/10/02)
A series of 10-membered cyclic 1,5-diynes has been prepared with arene rings fused at positions C-3/C-4.The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit.Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-1,4-diyl formation, the hydroquinone derivatives were much less reactive compared to the corresponding quinones.Substituents such as propargylic hydroxyl or keto group have a small but significant activating effect.The parent 3,4-benzo-1,8-decadiyne shows a half-life for rearrangement of 24 h at 84 deg C while the corresponding alkene, cyclodec-3-ene-1,5-diyne is reported to have a half-life of 18 h at 37 deg C.
Arene 1,4-diradical formation from o-dialkynylarenes
Semmelhack,Neu, Thomas,Foubelo, Francisco
, p. 3277 - 3280 (2007/10/02)
A series of five arene and quinone derivatives with dialkynyl substituents in the ortho positions and fixed in a 10-membered ring were prepared and tested with respect to thermal rearrangement to the corresponding arene 1,4 diradicals.
