Bicyclonon-1-ene: Matrix Isolation and Spectroscopic Characterization of a Moderately Strained Bridgehead Olefin

Article abstract of DOI:10.1021/jo00066a018

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.