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Creators/Authors contains: "Hatano, Sayaka"

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  1. ; ; ( , Australian Journal of Chemistry)
    Photolysis of exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclopropan-1-ol and exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclobutan-1-ol in benzene-d6 produces (1-hydroxycyclopropyl)- and (1-hydroxycyclobutyl)carbene respectively. It was observed that (1-hydroxycyclopropyl)carbene rearranges to cyclobutanone whereas (1-hydroxycyclobutyl)carbene forms cyclopentanone. Formation of both ketones is attributed to tautomerization of the corresponding enols that arise from ring expansion of the carbenes. Products assignable to intramolecular C–H insertions were not detected in the photolysates. 
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  2. ; ; ; ; ( , Journal of Physical Organic Chemistry)

    Broadband irradiation of 3,5‐diphenylisoxazole1in an argon matrix results in formation of azirine3. Further irradiation of the matrix reduces the amount of azirine3with concurrent formation of ylide4. Thus, it is theorized that the conversion of isoxazole1to azirine3goes through a triplet vinylnitrene2that does not intersystem cross to ketenimine6. Hence, the reactivity of triplet vinylnitrene2is different from similar vinylnitrene intermediates with α‐methyl substituents that intersystem cross to form corresponding ketenimines. Density functional theory calculations support the notion that the conjugation of the α‐phenyl group to the vinylnitrene moiety in vinylnitrene2renders it more flexible than vinylnitrenes with α‐methyl substituents, and therefore, vinylnitrene2intersystem crosses to azirine3, rather than ketenimine6. Copyright © 2016 John Wiley & Sons, Ltd.

     
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