Engineering reactions in crystals: suppression of photodecarbonylation by intramolecular β-phenyl quenching |
| |
| Authors: | Danny Ng Zhe Yang Miguel A Garcia-Garibay |
| |
| Affiliation: | aDepartment of Chemistry, University of California, Los Angeles, CA 90095-1569, USA |
| |
| Abstract: | The photochemical reactivity of cis- and trans-2-(p-carboxybenzyl)-2,6-diphenyl-6-vinylcyclohexanone, cis-1 and trans-1, was investigated in solution and in the crystalline solid state. Photochemical decarbonylation in solution proceeded in excellent yields to give cis- and trans-1-(p-carboxybenzyl)-1,2-diphenyl-2-vinylcyclopentanes cis-2 and trans-2 along with 3-(p-carboxybenzyl)-1,3-diphenylcycloheptene 3. Reactions in crystals were suppressed by a stereospecific quenching interaction between the benzyl substituent and the carbonyl oxygen in the crystalline ketone. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
