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Cyclopropanimines by Photolysis of Pyrazolinimines; Thermal Reaction of an Excited State

✍ Scribed by Prof. Dr. Helmut Quast; Dipl.-Chem. Andreas Fuss; Dr. Alfred Heublein

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
222 KB
Volume
19
Category
Article
ISSN
0044-8249

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✦ Synopsis

oxide (Zb) in 68% yield after chromatography (silica gel/ CH2C12) as colorless needles, m.p. 125-127 "C. On heating (190OC in toluene, 1 h, sealed tube), (Zb) gave (lb) in 44% yield after chromatography (silica gel/l : 1 CHCl3/n-C5HI2) as colorless plates, m. p. 66-67 "C (1 :2 CH2C12/ether). The I3C-NMR spectrum reveals seven distinct carbon atoms, which is only consistent with the unsymmetrical structure anti,anti-Trioxide (lc) (sequence A, B, C): The [2 + 61-endoperoxide (S), obtained alongside (3) on photo-oxygenation of (6)[2"1, served as starting point for the preparation of (lc). On thermolysis, but more conveniently on photolysis at h = 350 nm in benzene, the syn-dioxide (2c) was obtained in 57% yield after chromatography (silica gel/CHC13), colorless needles, m. p. 55-56 "C (2: 1 n-hexane/ether). Inspection of Dreiding models suggested that peracid epoxidation should take place preferentially anti to the existing epoxide rings because syn approach appears to be blocked by the endo-me-0::::

' "' 6 (Ib)

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