28682-57-7

Upstream product

• 14224-99-8 2-methyl-4,5-diphenyloxazole 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 1638-63-7 2-acetoxy-2-phenylacetyl chloride 
• 29071-09-8 2-acetoxy-2-phenylacetic acid 

Downstream Products

• 92126-06-2 2-methyl-3,4-bis(hydroxymethyl)-5-phenylfuran bis(methylcarbamate) 
• 92126-08-4 (4-Hydroxymethyl-5-methyl-2-phenyl-furan-3-yl)-methanol 

Relevant 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

(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.

Stereoselective synthesis of 2-aryltetrahydrofuran-3,4-dicarboxylate derivatives: Efficient approach to tetrahydrofuran lignans

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