| dc.contributor.author | Cristol, Stanley | en_US |
| dc.contributor.author | Harrington, J. Kenneth | en_US |
| dc.contributor.author | Morrill, Terence | en_US |
| dc.contributor.author | Greenwald, Brian | en_US |
| dc.date.accessioned | 2006-07-19T18:38:16Z | en_US |
| dc.date.available | 2006-07-19T18:38:16Z | en_US |
| dc.date.issued | 1971-09-24 | en_US |
| dc.identifier.citation | The Journal of Organic Chemistry 36N19 (1971) 2773-2776 | en_US |
| dc.identifier.issn | 1520-6904 | en_US |
| dc.identifier.uri | http://hdl.handle.net/1850/2137 | en_US |
| dc.description.abstract | Addition of hydrogen chloride to tetracyc10[3.2.0.0^2,7.0^4,6] heptane-l15-dicarboxylic acid (1, quadricyclenedicarboxylic acid) under various conditions results in two products, exo-5-chlorotricyclo[2.2,1.0^2,6] heptane-2,endo-3-dicarboxylic acid (4a) and exo-5-chlorotricyclo[2.2.1.0^2,6] heptane-2,exo-3-dicarboxylic acid (4b). Thus with this cyclopropane ring, cleavage by nucleophile proceeds by inversion and (effective) addition of electrophile proceeds by a combination of retention and inversion. The results are interpreted in terms of a homoconjugate addition process. | 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.relation.ispartofseries | Bridged Polycyclic Compounds | en_US |
| dc.relation.ispartofseries | LXXI | en_US |
| dc.subject | Cyclopropane ring | en_US |
| dc.subject | Homoconjugate addition process | en_US |
| dc.title | Stereochemistry and mechanisms of cyclopropane ring cleavage. Addition of hydrogen chloride to tetracyclo[3.2.0.02,7.04,6]heptane-1,5-dicarboxylic acid (quadricyclenedicarboxylic acid) | en_US |
| dc.type | Abstract | en_US |
| dc.identifier.url | http://dx.doi.org/10.1021/jo00818a010 | |
