Unexpected reactivity of 10-hydroxycamphor under triflic anhydride treatment: formation of a C-2-pseudosymmetric camphor-derived sulfite
| Autor: | T. de las Casas Engel, A. Garcia Martinez, C. Díaz Morillo, S. De La Moya Cerero, E. Teso Vilar, B. Lora Maroto, A. Garcia Fraile |
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| Zdroj: | ResearcherID ARKIVOC, Vol 2010, Iss 3, Pp 15-22 (2009) |
| Popis: | Treatment of enantiopure 10-hydroxycamphor with triflic anhydride and triethylamine yields enantiopure bis(10-camphoryl) sulfite, a novel interesting camphor-based C2-pseudosymmetric chiral sulfite with a prochiral sulfonyl group. The process takes place by initial formation of 10camphoryl triflinate, which undergoes an unexpected nucleophilic substitution with displacement of trifluoromethyl anion (attack of a second equivalent of 10-hydroxycamphor on the sulfur atom). The mentioned pseudosymmetric sulfite has also been obtained by standard reaction of 10-hydroxycamphor with thionyl chloride. |
| Databáze: | OpenAIRE |
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