Unexpected reactivity of 10-hydroxycamphor under triflic anhydride treatment: formation of a C-2-pseudosymmetric camphor-derived sulfite

作者：Garcia Martinez Antonio; Teso Vilar Enrique; Garcia Fraile Amelia; de la Moya Cerero Santiago; Lora Maroto Beatriz; Diaz Morillo Cristina; de las Casas Engel Tomas

来源：ARKIVOC, 2010, 15-22.

• Triflic anhydride
• camphor derivatives
• chiral sulfites
• triflinates

Treatment of enantiopure 10-hydroxycamphor with triflic anhydride and triethylamine yields enantiopure bis(10-camphoryl) sulfite, a novel interesting camphor-based C-2-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.

• 出版日期2010