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- Title
Unexpected reactivity of 10-hydroxycamphor under triflic anhydride treatment: formation of a C<sub>2</sub>-pseudosymmetric camphor-derived sulfite.
- Authors
Martínez, Antonio García; Vilar, Enrique Teso; Fraile, Amelia García; Cerero, Santiago de la Moya; Maroto, Beatriz Lora; Morillo, Cristina Díaz; Engel, Tomás de las Casas
- Abstract
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 10-camphoryl 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.
- Subjects
ANHYDRIDES; ETHYLAMINES; RING formation (Chemistry); SULFITES; SYMMETRY (Physics); CHIRALITY; NUCLEOPHILIC reactions
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2010, p15
- ISSN
1551-7004
- Publication type
Article