Ms. Gudipati et al., BICYCLO[3.2.2]NON-1-ENE - MATRIX-ISOLATION AND SPECTROSCOPIC CHARACTERIZATION OF A MODERATELY STRAINED BRIDGEHEAD OLEFIN, Journal of organic chemistry, 58(14), 1993, pp. 3668-3674
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-yldiaz
omethane and its photorearrangement product, 3-(bicyclo[2.2.2]oct-1-yl
)diazirine. It was characterized by IR and UV absorption and by H-1 an
d C-13 NMR spectroscopy. Further evidence for the proposed structure w
as provided by self-trapping and by the spectral effects of deuteratio
n on the olefinic carbon. Observed IR spectra and isotopic shifts agre
e well with the results of semiempirical (MNDO) and ab initio (SCF/6-3
1G) calculations.