84269-36-3Relevant academic research and scientific papers
Reaction of electron-deficient N=N, N=O double bonds, singlet oxygen, and CC triple bonds with acyloxyketenes or mesoionic 1,3-dioxolium-4-olates: Generation of unstable mesoionic 1,3-dioxolium-4-olates from acyloxyketenes
Hamaguchi, Masashi,Tomida, Naoki,Iyama, Yuji
, p. 1326 - 1334 (2007/10/03)
(Chemical Equation Presented) Reactions of azodicarboxylates and nitrosobenzene derivatives with acyloxyketenes generated from dehydrochlorination of α-acyloxyarylacetyl chlorides were carried out to give triacylbenzamidine and N-arylimide derivatives, respectively, in good yields. The same compounds were obtained from the reaction with mesoionic 1,3-dioxolium-4-olates generated by Rh2(OAc)4-catalyzed decomposition of aryldiazoacetic anhydride derivatives. Formation of the same compounds from the different starting materials indicates that their reactions involve the same intermediates. The formation of triacylbenzamidine and N-arylimide derivatives is explained by 1,3-dipolar cycloaddition between electron-deficient N=N or N=O bonds and mesoionic 1,3-dioxolium-4-olates following by decarboxylation, ring opening of the resultant carbonyl ylides, and subsequent Mumm rearrangement of the corresponding imidates. The reaction with singlet oxygen composed of more electronegative atoms than N=N and N=O bonds also gave products arising from the singlet oxygen adducts with 1,3-dioxolium-4-olates. The generation of less stable mesoionic 1,3-dioxolium-4-olates from acyloxyketenes was also confirmed by isolation of furandicarboxylates on generation of acyloxyketenes from α- acyloxyarylacetyl chlorides in the presence of reactive dipolarophile dimethyl acetylenedicarboxylate.
Reaction of nitrous oxide with cyclopentadienyl complexes of cobalt, rhodium, and titanium
Leont'ev,Fomicheva,Proskurnina,Zefirov
, p. 496 - 498 (2007/10/03)
The reaction of nitrous oxide with some cyclopentadienyl compounds of cobalt, rhodium, and titanium was studied. The corresponding furans were obtained in low to moderate yields.
Stereoselective synthesis of 2-aryltetrahydrofuran-3,4-dicarboxylate derivatives: Efficient approach to tetrahydrofuran lignans
Pei,Pei,Li,Ye
, p. 2069 - 2077 (2007/10/03)
A convenient and stereoselective synthetic route to the precursor of natural products, lignans, containing tetrahydrofuran has been developed. A series of asymmetric 2-aryltetrahydrofuran-3,4-carboxylic acid derivatives were synthesized in high yields wit
PHOTOSENSITIZED Oxidation of Furans. Part 4. Influence of the Substituents on the Behaviour of the endo-Peroxides of Furans
Graziano, M. Liliana,Iesce, M. Rosaria,Scarpati, Rachele
, p. 2007 - 2012 (2007/10/02)
A comparison of the ehaviour of endo-peroxides of the β-furoic esters (1a, b and d-f) and of the furans (1c or g), with the same 2,5-substituents, shows that the thermal instability of these compounds is related to the electron density in the bicyclic unsaturated ring.This also accounts for the higher stability of the alkyl-substituted endo-peroxides (1a-c) as compared with that of the aryl-substituted derivatives (1d-g), as well as for the different course of the thermal conversion in the two series.
