144342-39-2Relevant academic research and scientific papers
3α-Acetoxy-6,6-dimethylbicyclo[3.1.1]heptane-2-spiro-1′- cyclopropane from nopylamine deamination
Abraham, Raymond J.,Jones-Parry, Richard,Giddings, Rodney M.,Guy, Jonathan,Whittaker, David
, p. 643 - 646 (2007/10/03)
Deamination of nopylamine hydrochloride with sodium nitrite in acetic acid yields nopyl chloride 8, nopyl acetate 1 (R = OAc), 2-(1-acetoxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene 9 and 3α-acetoxy-6,6-dimethylbicyclo[3.1.1]heptane-2-spiro-1′-cyclopropane 12. The products are consistent with initial formation of a diazonium ion which reacts by nucleophilic attack, hydride shift or by shift of electrons of the double bond. The reaction is contrasted with the acetolysis of nopyl toluene-p-sulfonate, which yields 8,8-dimethyltricyclo[4.2.1.03,7]nonan-6-ol as the main product. The difference is suggested to result from the transition state being reached early (deamination) or late (toluene-p-sulfonate acetolysis) on the reaction coordinate.
Preparation of Campholenal Analogues: Chirons for the Lipophilic Moiety of Sandalwood-Like Odorant Alcohols
Chapuis, Christian,Brauchli, Robert
, p. 1527 - 1546 (2007/10/02)
In connection with structure-activity relationship studies, analogues of campholenal ((+)-4b), an important building block for sandalwood-like odorants, were prepared.The five-membered-ring analogues 4 were obtained by epoxidation of the corresponding α-pinene derivatives 2, followed by catalytic ZnBr2 isomerisation (Scheme 2).The six-membered-ring skeleton was obtained by ozonolysis of α-campholenyl acetate ((-)-14b), followed by intramolecular aldol condensation (Scheme 5). 13C-NMR assignments are given.
