Synthesis and Ritter reaction of 2,5,5,6-tetramethylbicyclo(2. 2. 1)heptan-2-endo-ol

Journal Article · Fri Dec 09 23:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5887794

Kozlov, N G; Popova, L A; Vyalimyae, T K; Knizhnikov, V A; Ol'dekop, Yu A

2,5,5,6-Tetrametbybicyclo(2.2.1)heptan-2-endo-ol is formed stereospecifically in the reaction of 5,5,6-trimethylbicyclo(2.2.1)heptan-2-one with methyllithium. The Ritter reaction of this tertiary alcohol with acetonitrile gave a mixture of 1,4,5,5-tetramethylbicyclo(2.2.1)hept-2-yl-exo-acetamide and 1,4,6,6-tetramethylbicyclo(2.2.1)hept-2-yl-exo-acetamide in a ratio of 2:1. A scheme including a series of rearrangements in the intermediate nonclassical carbocation is proposed for the Ritter reaction.

• Research Organization: Institute of Physical Organic Chemistry, Minsk (USSR)
• OSTI ID: 5887794
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:7; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETONITRILE
ALCOHOLS
ALKALI METAL COMPOUNDS
ALKANES
ALUMINIUM COMPOUNDS
ALUMINIUM HYDRIDES
AMIDES
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CONFORMATIONAL CHANGES
CYCLOALKANES
HYDRIDES
HYDROCARBONS
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INFRARED SPECTRA
INORGANIC ACIDS
ISOMERIZATION
KETONES
LITHIUM COMPOUNDS
LITHIUM HYDRIDES
NITRILES
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
SEPARATION PROCESSES
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS