20051-72-3Relevant academic research and scientific papers
Heterolytic Cleavage of Homoallylic Alcohols: Part II - Synthesis of 6-Hydroxycamphene, 4-Hydroxylongifolene and Corresponding Cyclopropylcarbinols from Tricyclene and Longicyclene
Patil, D. G.,Yadav, J. S.,Chawla, H. P. S.,Dev, Sukh
, p. 189 - 192 (2007/10/02)
Syntheses of 6-hydroxycamphene (1) and tricyclenol (5) from tricyclene (3) and 4-hydroxylongifolene (2) and ω-longifolol (6) from longicyclene (4) are reported.The formation of these has been rationalised.
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.
Methylcyclopropane - Soft Acid Reaction : Part I - Novel Lead Tetraacetate Oxidation of Longicyclene/Cyclene
Suryawanshi, S. N.,Nayak, U. R.
, p. 1 - 4 (2007/10/02)
In a novel lead tetraacetate (LTA) oxidation of the methylcyclopropane moiety in longicyclene (2), the elusive "true" longicamphor (3) (10-ketolongibornane) has been generated for the first time.Furthermore, the homoenol --> homoketone mechanistic pathway has also been established for the LTA/base transformation of longicyclene (2)/cyclene (6) to longicamphor (3)/camphor (7) by actual isolation of the intermediate homoenolacetate in either case.That longicamphor (3) is truly the "longi" homologue of the monoterpenoid camphor has been convincingly proved by the positive response of 3 to two key raections of 7.
