Ritter reactions. Part 14. Rearrangement of 3,3,7,7-tetramethyl-6-methylidenebicyclo[3.3.1]nonan-2-one

Authors
Djaidi, D Leung, ISH Bishop, R Craig, DC Scudder, ML
Citation
D. Djaidi et al., Ritter reactions. Part 14. Rearrangement of 3,3,7,7-tetramethyl-6-methylidenebicyclo[3.3.1]nonan-2-one, J CHEM S P1, (13), 2000, pp. 2037-2042
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
13
Year of publication
2000
Pages
2037 - 2042
Database
ISI
SICI code
1470-4358(2000):13<2037:RRP1RO>2.0.ZU;2-W
Abstract
When the bicyclic ketone 1 is reacted with concentrated sulfuric acid and a cetonitrile a complex sequence of reactions ensues. The compounds 2-6 are f ormed, with several of these being obtainable in good yields through carefu l control of the reaction conditions. X-Ray crystallography was used to det ermine unambiguously the structures of 4-6. These molecular conversions inv olve both rearrangement and Ritter reactions, and mechanistic explanations are proposed.