82053-85-8Relevant articles and documents
Longifolene-Derived Amines: A Comparative Hofmann Elimination Study with Isolongifolic Acid and Homoisolongifolic Acid as Precursors
Shitole, H. R.,Nayak, U. R.
, p. 88 - 90 (2007/10/02)
Isolongifolic acid (2) and homoisolongifolic acid (3) have been transformed into the C15- and C16-N,N-dimethylamino derivatives (8) and (9), respectively.A comparative Hofmann elimination study has revealed that, although both 8 and 9 possess a β-hydrogen available for elimination, the product-outcome is significantly different in the two cases; the major compound in the case of 8 arises from a reversal of the quaternary base to the parent dimethylamine (54percent) although a trivial amount (10percent) of the expected longifolene is also formed; on the other hand, 9 generates the theoretically anticipated vinylnorlongifolane (13) in 37 percent yield comparable with that of the dimethylamine (9) (33percent).Pb(IV)-Cu(II) reaction on the primary acid (3) fails to give longifolene by oxidative decarboxylation.