An interesting fragmentation during the thermoiysis of azido isoxazoles
TL;DR: In this article, it was found that the thermolysis of azido isoxazoles has been found to give cinnamoyl cyanides formed by facile fragmentation of the azoxazole ring.
Abstract: Thermolysis of azido isoxazoles has been found to give cinnamoyl cyanides formed by facile fragmentation of the isoxazole ring.
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TL;DR: In this paper, a regioselective synthesis of the title isoxazoles and pyrazoles through cyclocondensation of oxoketene dithioacetals with either hydroxylamine or hydrazine hydrate under controlled conditions is reported.
Abstract: The regioselective synthesis of the title isoxazoles and pyrazoles through cyclocondensation of oxoketene dithioacetals with either hydroxylamine or hydrazine hydrate under controlled conditions is reported.
5 citations
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TL;DR: Density functional theory (DFT) and complete active space self-consistent field (CASSCF) calculations were used to aid the characterization of nitrosoalkene 3 and to support the proposed mechanism for its formation.
Abstract: To enhance the versatility of organic azides in organic synthesis, a better understanding of their photochemistry is required. Herein, the photoreactivity of azidoisoxazole 1 was characterized in cryogenic matrices with IR and UV-Vis absorption spectroscopy. The irradiation (λ = 254 nm) of azidoisoxazole 1 in an argon matrix at 13 K and in glassy 2-methyltetrahydrofuran (mTHF) at 77 K yielded nitrosoalkene 3. Density functional theory (DFT) and complete active space self-consistent field (CASSCF) calculations were used to aid the characterization of nitrosoalkene 3 and to support the proposed mechanism for its formation. It is likely that nitrosoalkene 3 is formed from the singlet excited state of azidoisoxazole 1 via a concerted mechanism or from cleavage of an intermediate singlet nitrene that does not undergo efficient intersystem crossing to its triplet configuration.
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