ω-Methylcamphene/ω,ω-Dimethylcamphene: Synthesis and Reactions
ω-Methylcamphene (8)/ω,ω-Dimethylcamphene (9) have been synthesized by two routes; (i) the Prins reaction on camphene (1)/ω-methylcamphene (8) and (ii) olefination with methylenetriphenylphosphorane of the aldehyde (17)/methyl ketone (24) followed by isomerization of the resulting hydrocarbon with N-lithioethylenediamine.Camphenilone (2) also undergoes a direct Wittig reaction with ethylidenephosphorane (27) yielding 8 (E/Z)-mixture but fails to react with isopropylidenephosphorane (28) in an attempt to generate 9.Camphene (1) and its ω-methyl homologues 8/9 undergo normal epoxidation with perbenzoic acid without excess consumption of peracid.Lewis acid-catalyzed rearrangement of the resulting epoxides 16/23/29 has also been studied.The Hg(OAc)2/NaCl reaction on 8 yields the crystalline ω-methyl-ω-mercurichloride (10) transformed by pyridine perbromide into the ω-bromo-ω-methylcamphene (11).
Lamture, J. B.,Nayak, U. R.
p. 853 - 858
(2007/10/02)
Ectocyclic Methylene-Manganic Acetate Reaction: A Comparative Study with Camphene/Longifolene
Manganic acetate oxidation has been extended to ectocyclic methylene bridged systems of the type exemplified by camphene (1) and longifolene (2).In the case of 2 the reaction is completely abnormal, resulting in ω-acetoxy-methylation of the olefin without any lactone formation at all.On the other hand, the camphene-Mn(III) acetate reaction yields a mixture of γ-lactone (4) (50percent) and ω-acetoxymethylcamphene (3) (20percent).
Goudgaon, N. M.,Nayak, U. R.
p. 955 - 956
(2007/10/02)
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