dc.contributor.author | Morrill, Terence | en_US |
dc.contributor.author | Greenwald, Brian | en_US |
dc.date.accessioned | 2006-07-19T18:39:04Z | en_US |
dc.date.available | 2006-07-19T18:39:04Z | en_US |
dc.date.issued | 1971-09-24 | en_US |
dc.identifier.citation | The Journal of Organic Chemistry 36N19 (1971) 2769-2773 | en_US |
dc.identifier.issn | 1520-6904 | en_US |
dc.identifier.uri | http://hdl.handle.net/1850/2139 | en_US |
dc.description.abstract | Addition of hydrogen chloride and deuterium chloride to bicyclo [2.2.1] heptadiene (I, norbornadiene) results in (unlabeled and labeled, respectively) exo-dehydronorbornyl chloride (III) and nortricyclyl chloride (IV). The ratio of III/IV varies from ,75-85%/25-15% depending upon the solvent and addendum. Labeled III is composed of 57% (+/- 1 %) exo-cis-3-deuterio-2-dehydronorbornyl chloride (IIIa) and 43% syn-7-deuterio-2exo-dehydronorbornyl chloride (IIIb). Addition of deuterium chloride and hydrogen chloride to tetracyclo-[3.2.0.0^2,7.0^4-,6]heptane (II, quadricyclene) gave (respectively, labeled and unlabeled) III and IV in ratios of 80-87% III/20-13% IV. Labeled III (from II) was composed of 58% (+/- l%) IIIa and 42% IIIb. The mechanism(s) of addition to I and II must be very similar and neither addition can involve a symmetrically bridged cation as the sole precursor to III. Ionic cleavage of the cyclopropane rings of II are by the inversion process only. | en_US |
dc.format.extent | 31371 bytes | en_US |
dc.format.mimetype | application/pdf | en_US |
dc.language.iso | en_US | en_US |
dc.publisher | The American Chemical Society: The Journal of Organic Chemistry | en_US |
dc.subject | Cyclopropane rings | en_US |
dc.subject | Ionic cleavage | en_US |
dc.subject | Stereochemistry | en_US |
dc.title | Stereochemistry and mechanisms of the addition of deuterium chloride to bicyclo[2.2.1]heptadiene (norbornadiene) and to tetracyclo[3.2.02,7.04,6]heptane (quadricyclene) | en_US |
dc.type | Abstract | en_US |
dc.identifier.url | http://dx.doi.org/10.1021/jo00818a009 | |