92897-91-1

Upstream product

• 92897-88-6 exo-4,8-diphenyl-3,5,10-trioxa-9-azabicyclo<5,3,0>dec-8-ene 
• 92897-88-6 endo-4,8-diphenyl-3,5,10-trioxa-9-azabicyclo<5,3,0>dec-8-ene 

Relevant academic research and scientific papers

PREPARATION AND PHOTOCHEMISTRY OF 3-METHOXYCARBONYL SUBSTITUTED CONDENSED ISOXAZOLINES

The 1,3-dipolar cycloaddition of methoxy- and ethoxycarbonylnitriloxide to 2,3- and 2,5-dihydrofuran, 2,3-dihydropyrane, 7-oxabicyclo-2-heptene, and 1,3-dioxep-5-ene derivatives is described.The condensed isoxazolines Ia, IIIa, Va, Vb are rearrange

PHOTO-INDUCED REARRANGEMENT OF ISOXAZOLINES - A PATHWAY TO 2,4,5,8-TETRAHYDRO-1,3-DIOXA-5-AZOCINE DERIVATIVES

4-R-Substituted-8-X-phenyl-3,5,10-trioxa-9-azabicyclodec-8-enes (X = H, 4-CH3, 4-OCH3, 4-Cl, 4-Br, 4-F, 3-NO2, 3-Cl, 3-Br) have been prepared by cycloaddition of substituted benzenenitriloxides with 2-R-substituted 1,3-dioxep-5-enes (R = H, CH3, C6H5).A mixture of the endo and exo adducts is formed, if R is CH3 or C6H5.Their irradiation produces high yields of the title compounds as the single products.High selectivity of the photo-rearrangement is due to resonance stabilization of the biradical with p electrons of the oxygen atom.The quantum yields of the photoreaction vary from 0.02 to 0.04 depending on the substituent X.An unexpected dependence has been found between the quantum yield of the photo-rearrangement and stereochemical arrangement of the 4-R-substituent: exo derivatives exhibit higher values than the endo derivatives.Also different are UV spectra of the endo and exo derivatives.A new synthesis principle is described enabling preparation of (n+1)-membered heterocycles from n-membered heterocycles.

PHOTOINDUZIERTE UMLAGERUNG VON ISOXAZOLINEN: SYNTHESEWEG ZU 2,4,5,8-TETRAHYDRO-1,3-DICX-5-AZOCINEN

A high yield 2,4,5,8-tetrahydro-1,3-diox-5-azocine synthesis, which employs a sequence of cycloaddition and photoinduced rearrangement has been developed.