4801-15-4Relevant articles and documents
Synthesis of naphthalenophane-type macrocyclic compounds using Mn(III)-based dihydrofuran-clipping reaction
Matsumoto, Chiaki,Yasutake, Ken-ji,Nishino, Hiroshi
, p. 6963 - 6971 (2016)
The Mn(III)-based oxidation of 2,7-, 1,8-, and 1,5-disubstituted naphthalenes bearing both the 1,4-dioxa-7,7-diphenylhep-6-enyl and 1,4-dioxa-5,7-dioxooctyl groups gave new [12]naphthalenophanes along with the corresponding diploids via assembly of the dihydrofuran ring. A similar reaction of the 2,6-disubstituted naphthalene having the same substituents did not produce the naphthalenophane, but the diploid, [12,12](2,6)naphthalenophane, was obtained in a small amount. The 2,6-disubstituted naphthalene tethered to the 1,4,7-trioxa-10,10-diphenyldec-9-enyl and 1,4,7-trioxa-8,10-dioxoundecyl groups also underwent the dihydrofuran-clipping reaction to afford a trace amount of the desired [18](2,6)naphthalenophane. The reaction details and the structure determination of the products are described.
Intramolecular Cyclization of 3,3-Diarylpropenylamides of Electron-Deficient Alkenes: Stereoselective Synthesis of Functionalized Hexahydrobenzo[f]isoindoles
Sugiura, Hirotaka,Yamazaki, Shoko,Go, Kakeru,Ogawa, Akiya
, p. 204 - 220 (2018/12/13)
Intramolecular Diels–Alder reactions of various 3,3-diarylpropenylamides of electron-deficient alkenes to give hexahydrobenzo[f]isoindoles were investigated. Reaction of 1,1,2-ethenetricarboxylic acid 1,1-diethyl ester with 3,3-diaryl-2-propen-1-amines under the amide formation conditions gave the tricyclic compounds in sequential processes involving intramolecular Diels–Alder reaction. The reaction gave cis- and trans-fused tricyclic compounds selectively, depending on the substituents on the benzene ring, reaction temperature and solvent. In the reaction with dissymmetrically substituted 3,3-diaryl-2-propen-1-amines, trans-substituted aryl group reacted mainly as a styrene component. Amides of electron-deficient alkenic carboxylic acids such as fumarate do not undergo cyclization at room temperature sequentially and the reaction on heating gave trans-fused hexahydrobenzo[f]isoindoles. The origin of the observed stereoselectivity has been examined by the DFT calculations.
Hydrodebromination of allylic and benzylic bromides with water catalyzed by a rhodium porphyrin complex
Yang, Wu,Chen, Chen,Chan, Kin Shing
supporting information, p. 12879 - 12883 (2018/10/02)
Hydrodebromination of allylic and benzylic bromides was successfully achieved by a rhodium porphyrin complex catalyst using water as the hydrogen source without a sacrificial reductant. Mechanistic investigations suggest that bromine atom abstraction via a rhodium porphyrin metalloradical operates to give the rhodium porphyrin alkyl species and the subsequent hydrolysis of the rhodium porphyrin alkyl species to a hydrocarbon product is a key step to harness the hydrogen from water.