20944-85-8Relevant articles and documents
A novel photorearrangement of aryl naphthylmethyl ethers. Formation of cyclohexa-2,4-dienone derivatives
Yoshimi, Yasuharu,Sugimoto, Akira,Maeda, Hajime,Mizuno, Kazuhiko
, p. 4683 - 4686 (1998)
Irradiation of a benzene solution containing 1-methoxycarbonyl-2- naphthylmethyl 2,6-dimethyl substituted phenyl ethers (1a,b) afforded cyclohexa-2,4-dienone derivatives (2a,b) as initial rearranged products via C-O bond cleavage and meta substituted phenols (3a,b) which were formed by subsequent photorearrangement of 2a,b.
Modular Dual-Tasked C-H Methylation via the Catellani Strategy
Gao, Qianwen,Shang, Yong,Song, Fuzhen,Ye, Jinxiang,Liu, Ze-Shui,Li, Lisha,Cheng, Hong-Gang,Zhou, Qianghui
supporting information, p. 15986 - 15993 (2019/10/11)
We report a dual-tasked methylation that is based on cooperative palladium/norbornene catalysis. Readily available (hetero)aryl halides (39 iodides and 4 bromides) and inexpensive MeOTs or trimethylphosphate are utilized as the substrates and methylating reagent, respectively. Six types of "ipso" terminations can modularly couple with this "ortho" C-H methylation to constitute a versatile methylation toolbox for preparing diversified methylated arenes. This toolbox features inexpensive methyl sources, excellent functional-group tolerance, simple reaction procedures, and scalability. Importantly, it can be uneventfully extended to isotope-labeled methylation by switching to the corresponding reagents CD3OTs or 13CH3OTs. Moreover, this toolbox can be applied to late-stage modification of biorelevant substrates with complete stereoretention. We believe these salient and practical features of our dual-tasked methylation toolbox will be welcomed by academic and industrial researchers.
Synthesis of pentacyclic compounds via intramolecular [3 + 2] photocycloaddition of cycloalkene linked naphthalenes
Maeda, Hajime,Uesugi, Tomoya,Fujimoto, Yasufumi,Mukae, Hirofumi,Mizuno, Kazuhiko
, p. 198 - 206 (2017/02/10)
Intramolecular photocycloaddition reactions of cycloalkene linked naphthalenes lead to formation of pentacyclic compounds in a high yielding and stereoselective manner. Intramolecular [2 + 2] cycloadducts are formed initially in photoreactions of cycloalkene linked 1-cyanonaphthalenes. The initially formed intramolecular [2 + 2] cycloadducts absorb light at wavelengths used to promote the photochemical reactions and, as a result, they undergo efficient photocycloreversion to regenerate the starting substrates. In a less efficient competing process, the cycloalkene linked 1-cyanonaphthalenes react to form [3 + 2] intramolecular photoadducts, which do not absorb incident light under the conditions used. Consequently, these photoadducts become the major products in these processes. The relative configuration of the major diastereomers of the pentacyclic products formed from photoreactions of cyclopentene linked naphthalenes (cis-cis) differ from those (cis-trans) arising from the cyclooctene linked substrates. The results of theoretical calculations, which show that steric factors govern the preferred facial mode of intramolecular addition, are in good agreement with the stereochemical course of these photoreactions.