BICYCLO[3.2.2]NON-1-ENE - MATRIX-ISOLATION AND SPECTROSCOPIC CHARACTERIZATION OF A MODERATELY STRAINED BRIDGEHEAD OLEFIN

Citation
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
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
58
Issue
14
Year of publication
1993
Pages
3668 - 3674
Database
ISI
SICI code
0022-3263(1993)58:14<3668:B-MASC>2.0.ZU;2-Z
Abstract
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.