5732-81-0Relevant articles and documents
Synthesis and Reactions of β-Camphole Compounds
Schulze, K.,Wyssuwa, K.,Trauer, H.,Habermann, A.-K.
, p. 537 - 543 (2007/10/02)
In contrast to the well known α-campholenic (B) and fencholenic compounds (C) little is known about β-campholenic derivatives (A) because of their difficult accessibility. β-Campholenic compounds (A) can be obtained: (1) by Baeyer-Villiger oxidation of camphor via lactone 7 and β-dihydrocampholenic lactone (5); (2) by Beckmann fragmentation of camphor oxime via α-(2) and β-campholenic nitril (3) and the lactone 5; and (3) by acid catalysed rearrangement of α-campholenic derivatives (B, 17a, b).The β-analogous brahmanol (14) can be synthesized by the reaction of the β-campholenic bromide (11) with methyl diethyl malonate or by r earrangement of brahmanol.
Ein neuer Zugang zum β-Campholensystem
Schulze, Klaus,Trauer, Heiner
, p. 59 - 60 (2007/10/02)
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One-Step Annelation. A Convenient Method for the Preparation of Diols, Spirolactones, and Spiroethers from Lactones
Canonne, Persephone,Foscolos, Georges B.,Belanger, Denis
, p. 1828 - 1835 (2007/10/02)
1-(ω-Hydroxyalkyl)cyclopentanols and -cyclohexanols were prepared in one step in high yields from butane-1,4-diyl- and pentane-1,5-diylmagnesium dibromides and lactones in tetrahydrofuran.This method was found to be general and applicable to lactones of any size (β, γ, δ, and ε) and structure whether aliphatic, aromatic, bicyclic, or spirocyclic.Evidently important steric hindrance close to the carbonyl group prevents annelation and attack on the second nucleophilic center of the Grignard reagent.Furthermore, in the case of oxetan-2-one one obtains, in additionto the corresponding diol, products resulting from scission of the C-O bond.The diols by appropriate transformation afford new routes to spirolactones and spiroethers.
