Synthesis and acid-catalyzed transformations of 1-(1,6,6-trimethylbicyclo(2. 1. 1)hex-5-yl)-1-alkanones and 1-(1,6,6-trimethylbicyclo-(2. 1. 1)hex-5-yl)-1-alken-1-ones

Journal Article · Mon Jun 20 00:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5971254

Volkova, O O; Cherkaev, G V; Novikov, N A; Erman, M B; Aul'chenko, I S; Mochalin, V B

The reaction of 1,6,6-trimethylbicyclo(2.1.1)hexane-5-carbaldehyde (photocitral B) with Grignard reagents followed by oxidation of the obtained alcohols gave 1-(1,6,6-trimethylbicyclo(2.1.1)hex-5-yl)-1-alkanones and 1-(1,6,6-trimethylbicyclo(2.1.1)hex-5-yl)-1-alken-1-ones, which isomerize to 1-(2,3,3-trimethyl-1-cyclopentenyl)-2-alkanones when heated in the presence of p-toluenesulfonic acid. It was shown that the intermediate compounds in this reaction are 1-(2,2,3-trimethyl-3-cyclopentenyl)-2-alkanones. Underanalogous conditions photocitral B isomerizes to /alpha/-campholenaldehyde.

• Research Organization: All-Union Scientific-Research Institute of Synthetic and Natural Perfumes, Moscow (USSR)
• OSTI ID: 5971254
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 24:1; Other Information: Translated from Zh. Org. Khim.; 24: No. 1, 135-142 (Jan 1988)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
KETONES
CATALYSIS
SULFONIC ACID ESTERS
CATALYTIC EFFECTS
ALCOHOLS
ALDEHYDES
CHROMATOGRAPHY
CYCLOALKANES
GRIGNARD REAGENTS
INFRARED SPECTRA
ISOMERIZATION
ISOMERS
NMR SPECTRA
ORGANIC POLYMERS
OXIDATION
REACTION INTERMEDIATES
SYNTHESIS
TEMPERATURE EFFECTS
ALKALINE EARTH METAL COMPOUNDS
ALKANES
CHEMICAL REACTIONS
ESTERS
HYDROCARBONS
HYDROXY COMPOUNDS
MAGNESIUM COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANOMETALLIC COMPOUNDS
POLYMERS
SEPARATION PROCESSES
SPECTRA
400201* - Chemical & Physicochemical Properties