539-80-0Relevant articles and documents
Radlick
, p. 960 (1964)
Garfunkel,Reingold
, p. 3725 (1979)
Mc Clelland et al.
, p. 970,971 (1979)
Tropone
Reingold,Kwong,Kahr,Menard,Cummings,Kowalski
, p. 1463 - 1466 (1993)
-
van Tamelen et al.
, p. 5442 (1956)
Harmon,K.M. et al.
, p. 2567 - 2568 (1968)
Kende,Chu
, p. 4837 (1970)
Organocatalytic stereoselective [8+2] and [6+4] cycloadditions
Mose, Rasmus,Preegel, Gert,Larsen, Jesper,Jakobsen, Sofie,Iversen, Eva H?gh,J?rgensen, Karl Anker
, p. 487 - 492 (2017)
Cycloadditions that involve more than six I € electrons are termed higher-order cycloadditions and are an excellent tool for solving complex synthetic challenges, as they provide direct access to polycyclic scaffolds that contain medium-sized rings. They have interesting synthetic potential for the discovery of new bioactive molecules and in natural product synthesis. It is peculiar that stereocontrolled [8+2] and [6+4] cycloadditions have been largely neglected for the past 50 years. Here we demonstrate a cross-dienamine activation of 2-cyclopentenone and the unprecedented endocyclic linear-dienamine activation of 2-cyclohexenones and 2-cycloheptenones. These dienamine intermediates undergo aminocatalytic stereoselective [8+2], [6+4] and formal [4+2] cycloadditions with various heptafulvenes. The periselectivities of the cycloadditions are controlled based on the ring size of the 2-cycloalkenones and the substitution patterns of the heptafulvenes. The chiral products obtained undergo various chemical and photochemical single-step transformations that give access to other classes of all-carbon polycyclic scaffolds.
DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene
Cheng, Dongping,Yu, Chenze,Pu, Yueqi,Xu, Xiaoliang
supporting information, (2022/01/23)
An efficient 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene is developed. It provides a variety of α-alkenylated 1,3-dicarbonyl compounds in moderate to good yields under mild conditions.
Dialkylated Dihydroazulene and Vinylheptafulvene Derivatives – Synthesis and Switching Properties
Lubrin, Nickie C. M.,Vlasceanu, Alexandru,Frandsen, Benjamin N.,Skov, Anders B.,Kilde, Martin Dr?hse,Mikkelsen, Kurt V.,Nielsen, Mogens Br?ndsted
supporting information, p. 2932 - 2939 (2017/06/06)
Functionalization of molecular photoswitches at specific positions offers a way of tuning their switching properties. The work presented here describes the development of a new protocol towards the synthesis and functionalization of the dihydroazulene/vinylheptafulvene (DHA/VHF) photo-/thermoswitch. The key step is a facile condensation reaction using a functionalized tropone derivative, and the new synthetic method was employed in the regioselective preparation of a novel dimethyl-substituted DHA photoswitch. This compound presents the first accessible derivative with alkyl groups on the seven-membered ring of the system ― at positions C5 and C7. From experimental and theoretical kinetics studies on the thermal VHF-to-DHA electrocyclic reaction, the influence of the electron-donating methyl groups was elucidated. In addition, we subjected a small selection of 4,8a-dialkylated compounds to a computational study to elucidate how steric interactions can alter the relative DHA–VHF stabilities. The synthetic methodology offers access to novel DHA scaffolds and substitution patterns, which in turn can lead to systems that can help to address broader questions concerning the potential applicability of the DHA/VHF system in the context of solar-thermal energy-storage systems or other photochromic applications.