13211-15-9Relevant articles and documents
A ONE-FLASK MULTICOMPONENT ANNULATION REACTION AS THE KEY STEP IN A TOTAL SYNTHESIS OF SPIROBICYCLIC (+/-)-β-VETIVONE
Posner, Gary H.,Shulman-Roskes, Ellen M.
, p. 4677 - 4686 (1992)
One flask, 3-component Michael-Michael-Dieckmann cyclizations are applied to 2+2+2 construction of spirobicyclic cyclohexanone β-keto esters 7 and 11 as pivotal intermediates for synthesis of naturally-occuring spirodecane β-vetivone (1).Some unexpected difficulties were encountered and are discussed.A novel BF3-promoted unidirectional dehydration of tertiary alcohol silyl ether 15 exclusively into isopropylidene cyclopentane 16 is reported.
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Huang et al.
, p. 3329 (1976)
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Enantiomer-differentiating Hydrogen Transfer from Fenchol to Menthone over Molten Indium Ctalyst
Sugawara, Hiroshi,Ogino, Yoshisada
, p. 1079 - 1086 (1982)
The inital rate (r0) of the hydrogen-transfer reaction from D-fenchol to menthone has been found to obey the following eqation r0,j = kjpA where k is the rate constant, pA is the partial pressure of D-fenchol, and the subscript j denotes any one of the optical isomers (L-, D- and D,L-) of menthone.The reaction is enantiomer-differentiating: kL > kD, and the optical resolution of D,L-menthone takes place in the reaction between D-fenchol and D,L-menthone.The experimental results are explained on the bases of an Eley-Rideal-type mechanism and stereochemically consistent transition-state models.Probable adsorption models for menthone are also proposed.
Ozonides of mono-, bi- and tricyclic terpenes
Griesbaum, Karl,Hilss, Michael,Bosch, Joachim
, p. 14813 - 14826 (2007/10/03)
Ozonolysis of (+)-limonene (1) afforded a monoozonide 2 by attack of ozone at the internal double bond and two diastereomeric diozonides (3). Ozonolysis of 1 on polyethylene gave diozonides 3, and ozonolysis on silica gel gave an epoxy ozonide 5. Ozonolyses of (-)-β-pinene (15), (+)-sabinene (20) and (+)-aromadendrene (23) gave two diastereomers, each, of the corresponding ozonides 16, 21 and 24, respectively. Ozonolysis of camphene (26) gave a very labile ozonide 27, while ozonolysis of (-)-α-pinene (12) gave no ozonide. Ozonolysis of (+)-limonene (1) in the presence of formaldehyde gave a cross-ozonide (4), derived from ozone cleavage of the internal double bond, and ozonolysis of (-)-β-pinene in the presence of acetaldehyde also gave a cross-ozonide (17).