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Reversal of Diastereoselectivity of Mesitonitrile Oxide 1,3-Dipolar Cycloadditions with Penta-1,4-diene-3-ol by Mg(II)

Micuch P., Fisera E., Cyrański M.

Polish Journal of Chemistry

2005

Vol. 79 / nr 1

65-72

1,3-Dipolar cycloadditions of mesitonitrile oxide (4) to penta-1,4-diene-3-ol (5) proceed regioselectively irrespective of the presence or absence of the Mg(II) additive. Addition of Grignard reagent reverses the diastereoselectivity of the cycloaddition. The reaction of mesitonitrile oxide with magnesium alkoxide of penta-1,4-diene-3-ol (5) proceeded with exclusive diastereoselectivity giving the syn 6b and 7c isomer of the resulting isoxazolines.

Crystal and molecular structure of 3-(2,4,6-trimethyl-phenyl)-8-phenyl-oxo-1,7-dioxa-2-azaspiro[4,4]non-2-ene

Anulewicz-Ostrowska R., Piętka E., Krygowski T., Micuch P., Fisera L.

Polish Journal of Chemistry

1999

vol. 73 nr 4

727-733

Crystal and molecular structure of 3-(2,4,6-Trimethylphenyl)-8-phenyl-oxo-1,7-dioxa-2-azaspiro[4,4]non-2-ene has been determined by X-ray diffraction technique. Crystal data for C21H21NO3: monoclinic, C2/c, a=20.969(4) A, b=10.319(2) A, c=16.601(3) A, b=97.5(3)0, Z=8, R=0.0658 for 3477 reflections. Contrary to the solution, in the crystalline state only one conformer exists.