19890-84-7Relevant academic research and scientific papers
Generation and Reaction of ω-Nitrolongifolene
Dalavoy, V. S.,Deodhar, V. B.,Nayak, U. R.
, p. 396 - 398 (2007/10/02)
A fairly satisfactory method for the generation of the elusive ω-nitrolongifolene (3) involves the action of nitrous acid generated in situ (aq.NaNO2 + AcOH) on longifolene (2).Unlike in the case of ω-nitrocamphene (4), which produces the cyclopropane acid (5) by the action of 98percent H2SO4, similar reaction on 3 fails to give any indentifiable product.Prolonged refluxing of 3 with aqueous ethanolic KOH/t-BuOK in t-BuOH yields only the starting material without any evidence of the formation of ketone (8) - in sharp contrast to the case of its monoterpene analog 4 which yields camphenilone (9) in excellent yield.On refluxing with KOH in ethylene glycol, however, 3 gives two products - the pseudolongifolic acid (1) and the primary alcohol (11) - obviously through the intermediacy of the cyclopropane aldehyde (10) which suffers a Canizzaro reaction under the strongly basic reaction conditions.
