Journal of Organic Chemistry p. 3668 - 3674 (1993)
Update date:2022-08-03
Topics:
Gudipati, Murthy S.
Radziszewski, Juliusz G.
Kaszynski, Piotr
Michl, Josef
Bicyclo<3.2.2>non-1-ene was generated in low-temperature matrices and in fluid solutions by photodecomposition of bicyclo<2.2.2>oct-1-yldiazomethane and its photorearrangement product, 3-(bicyclo<2.2.2>oct-1-yl)diazirine.It was characterized by IR and UV absorption and by 1H and 13C NMR spectroscopy.Further evidence for the proposed structure was provided by self-trapping and by the spectral effects of deuteration on the olefinic carbon.Observed IR spectra and isotopic shifts agree well with the results of semiempirical (MNDO) and ab initio (SCF/6-31G*) calculations.
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