22841-82-3Relevant academic research and scientific papers
Studies of Chrysanthemic Acid Derivatives: Catalyses Reactions of 3-(2-Hydroxymethyl-3,3-dimethylcyclopropyl)-2-methylpropanol and Formation of a Novel Eight-membered Cyclic Sulphite
Crammer, Bernard,Goldschmidt, Zeev,Ikan, Raphael,Cohen, Shmuel
, p. 887 - 891 (2007/10/02)
Acid catalysed reaction of the cyclopropanediol (3) derived from cis-chrysanthemic acid cis-(1) afforded, depending on the reaction conditions, 3-vinyl-2,2,5,5-tetramethyltetrahydrofuran (4) and 4,4,7,7-tetramethyl-3-oxabicycloheptane (5).On treatment with thionyl chloride-pyridine complex there was obtained in addition the eight-membered cyclic sulphite, 6,6,9,9-tetramethyl-3,5-dioxa-4-thiabicyclononane 4-oxide (6).X-Ray analysis confirms a boat-chair conformation with the S=O group trans to the cyclopropane ring in an equatorial situation.Thermal reaction of (6) gave either (4) or a mixture of (5), cis-chrysanthemol (7), and cis-isochrysanthemol (8).
STEREOSPECIFIC CYCLOPROPENIC SYNTHESIS OF CIS-CHRYSANTHEMIC METHYL ESTER. 2. THE BY-PASSING DIAZOALKANE WAY (1).
Franck-Neumann, M.,Miesch, M.
, p. 1409 - 1412 (2007/10/02)
A stereospecific synthesis of cis-chrysanthemate by catalytic hydrogenation of a cyclopropene is described.The required precursor, a 3H-pyrazole, is obtained here via a novel dianion reaction and MnO2 dehydrogenation of a Δ2-pyrazoline, instead of the more cumbersome diazoaddition method.
Addition of Organomagnesium Halides to C = C Bonds, XVI. - A Synthetic Route to Chrysanthemic Acid
Lehmkuhl, Herbert,Mehler, Klaus
, p. 2244 - 2246 (2007/10/02)
Addition of 1-isobutenylmagnesium bromide (4) to 3,3-dimethylcyclopropene leads to the formation of a 1:1 product as well as considerable amounts of 1:2, 1:3, and higher molecular adducts.Further reaction with carbon dioxide gives, after hydrolysis, a mixture of cis-chrysanthemic acid (6; 39percent) and the higher molecular acids 1 and 2.
