109258-04-0Relevant academic research and scientific papers
Iron-doped single-walled carbon nanotubes as new heterogeneous and highly efficient catalyst for acylation of alcohols, phenols, carboxylic acids and amines under solvent-free conditions
Sharghi, Hashem,Jokar, Mahboubeh,Doroodmand, Mohammad Mahdi
experimental part, p. 426 - 442 (2011/04/15)
Iron-doped single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated adducts in good to excellent yields.
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.
