13674-44-7Relevant academic research and scientific papers
Thallium trinitrate mediated oxidation of 3-alkenols: Ring contraction vs cyclization
Ferraz, Helena M. C.,Longo Jr., Luiz S.,Zukerman-Schpector, Julio
, p. 3518 - 3521 (2007/10/03)
The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.
Design, synthesis and structure-odor correlation of novel spiro[4.5]-decan-2-ones
Kraft, Philip,Cadalbert, Riccardo
, p. 2243 - 2253 (2007/10/03)
Dehydration and Rupe rearrangement of 2-(3,3-dimethylcyclohexyl)hex-3-yne-2,5-diol (9) furnished as a 3% byproduct the intense vetiver-like smelling 4,7,7-trimethyl-1-methylene-spiro[4.5]decan-2-one (11). Motivated by the commercial importance of vetiver oil and the lack of synthetic substitutes as well as the lack of insight into the structural requirements for vetiver odorants, an efficient synthetic route to vetiver-like smelling compounds was developed. It consists of Wittig-Horner-Emmons reaction of diverse cycloalkanones with triethyl 2-phosphonopropionate, subsequent Grignard reaction with in situ conversion to the trienolate, and classical Nazarov cyclization of the resulting dienones. This route not only leads to 11 in 61% yield in the final Nazarov cyclization, but also to 16 analogs, which provide insight into both, the Nazarov reaction and the structure-odor relationship of vetiver odorants. Other vetiver-like smelling compounds discovered include (1RS,4SR,5SR)-1,4,7,7-tetramethylspiro[4.5]decan-2-one (16), 4-methyl-1-methylenespiro[4.6]undecan-2-one (30) and 4-methyl-1-methylenespiro[4.7]dodecan-2-one (31).
