Formation of 3-methyl-1-adamantyl trifluoromethanesulfonate in the reaction of 3,7-dimethylenebicyclo[3.3.1]nonane with trifluoromethanesulfonic acid. Dissociation and carbocationic rearrangements

Formation of 3-methyl-1-adamantyl trifluoromethanesulfonate in the reaction of 3,7-dimethylenebicyclo[3.3.1]nonane with trifluoromethanesulfonic acid. Dissociation and carbocationic rearrangements Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2002, Volume: 38, Number: 7, Pages: 1009-1013 Pages count : 5 DOI: 10.1023/A:1020805713351

Authors

Genaev AM ¹ , Sokolenko VA ² , Sal'nikov GE ¹ , Mamatyuk VI ¹ , Shubin VG ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Div, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Siberian Div, Inst Chem & Chem Technol, Moscow 117901, Russia

According to the H-1 NMR data, the reaction of equimolar amounts of 3,7-dimethylenebicyclo-[3.3.1]nonane with trifluoromethanesulfonic acid in CD2Cl2 leads to formation of 3-methyl-1-adamantyl trifluoromethanesulfonate. Further addition of trifluoromethanesulfonic acid promotes partial dissociation of 3-methyl-1-adamantyl trifluoromethanesulfonate into 3-methyladamantyl cation and trifluoromethanesulfonate anion, and the cation undergoes fast pericyclic rearrangement involving migration of bridgehead hydrogen atoms to the cationic center.

Genaev A. , Sokolenko V. , Sal'nikov G. , Mamatyuk V. , Shubin V.
Formation of 3-methyl-1-adamantyl trifluoromethanesulfonate in the reaction of 3,7-dimethylenebicyclo[3.3.1]nonane with trifluoromethanesulfonic acid. Dissociation and carbocationic rearrangements
Russian Journal of Organic Chemistry. 2002. V.38. N7. P.1009-1013. DOI: 10.1023/A:1020805713351 WOS Scopus РИНЦ

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