675825-21-5Relevant articles and documents
Bidirectional Synthesis, Photophysical and Electrochemical Characterization of Polycyclic Quinones Using Benzocyclobutenes and Benzodicyclobutenes as Precursors
Mohamed Abdelmoniem, Amr,Abdelshafy Abdelhamid, Ismail,Butensch?n, Holger
, p. 6319 - 6333 (2021)
Quinones have widespread applications in view of their interesting chemical and photophysical features. On the other hand, benzocyclobutenes (BCBs) are generally masked reactive dienes suitable for the [4+2] cycloaddition reactions. Here, benzocyclobutenes and benzodicyclobutenes (BDCBs) were prepared and further reacted with benzoquinone and naphthoquinone in order to obtain some new polycyclic quinones with highly extended π systems, namely, 6-bromo-5,8-dimethoxyanthracene-1,4-dione, 2,9-dibromo-1,4,8,11-tetramethoxypentacene-6,13-dione, 9-bromo-7,10-dimethoxytetracene-5,12-dione, 3,10-dimethoxycyclobuta[b]anthracene-1,5,8(2H)-trione, 6,10,17,21-tetramethoxynonacene-1,4,8,12,15,19-hexaone, and 3,12-dimethoxycyclobuta[b]tetracene-1,5,10(2H)-trione. In addition to their spectroscopic characterization the new compounds are investigated by UV and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations.
Allylic vs. Vinylic Deprotonation Reactions of Cyclic Vinyl Ethers. 7-Lithio-2,3,4,5-tetrahydrooxepin: Synthesis and Carbon-13 Nuclear Magnetic Resonance Spectrum
Oakes, Fred T.,Yang, Fu-An,Sebastian, John F.
, p. 3094 - 3097 (2007/10/02)
2,3,4,5-Tetrahydrooxepin treated with either n-butyllithium or tert-butyllithium affords 7-lithio-2,3,4,5-tetrahydrooxepin.The question of allylic vs. vinylic deprotonation of cyclic vinyl ethers was examined by varying ring size and degree of unsaturation.Carbon-13 spectral data for the anions obtained from 2,5-dihydrofuran, 2,3-dihydrooxepin, and 2,3,4,5-tetrahydrooxepin are reported.In contrast to 2,3,4,5-tetrahydrooxepin, 2,3-dihydrooxepin undergoes allylic deprotonation, possibly as a result of a slightly larger C-C=C bond angle in the dihydrooxepin as compared to that of the tetrahydrooxepin.