1773-40-6Relevant academic research and scientific papers
Cyclopropylmethyl- and cyclobutylmethyllithium by an arene-catalyzed lithiation. Stability and reactivity
Pe?afiel, Itziar,Pastor, Isidro M.,Yus, Miguel
experimental part, p. 2928 - 2935 (2010/06/16)
The reaction of (chloromethyl)cyclopropane 5 and (bromomethyl)cyclobutane 8 with lithium and a substoichiometric amount of DTBB, in the presence of different carbonyl compounds as electrophiles, in THF at -78 °C leads, after hydrolysis, to the corresponding cycloalkyl alcohols 6 and 9, respectively. However, when the same starting materials are lithiated using naphthalene as catalyst in diethyl ether and at higher temperature (0 or 25 °C), and then react with the same electrophiles, the final hydrolysis yields the corresponding unsaturated alcohols 7 and 10, respectively.
Easy selective generation of (lithiomethyl)cyclopropane or homoallyllithium by a chlorine-lithium exchange
Pastor, Isidro M.,Pe?afiel, Itziar,Yus, Miguel
scheme or table, p. 6870 - 6872 (2009/04/07)
The reaction of (chloromethyl)cyclopropane 5 with lithium and a catalytic amount of DTBB (5 mol %) in the presence of different carbonyl compounds [Et2CO, n-Pr2CO, (c-C3H5)2CO, (CH2)5CO, PhCOMe, t-BuCHO, i-PrCHO, PhCHO] as electrophiles in THF at -78 °C leads, after hydrolysis with water, to the corresponding cyclopropyl alcohols 6. However, when the same starting material is lithiated using naphthalene as the arene catalyst in ether at 0 °C and then reacts with the same series of electrophiles, the final hydrolysis with water yields the corresponding unsaturated alcohols 7.
A General Approach to the Synthesis of Butanolides: Synthesis of the Sex Pheromone of the Japanese Beetle
Baskaran, Sundarababu,Islam, Imadul,Chandrasekaran, Srinivasan
, p. 891 - 895 (2007/10/02)
A variety of substituted γ-hydroxy olefins 1 have been converted to butanolides 4 in very high yield in a three-step sequence involving bromoetherification, elimination, and oxidative cleavage.The key step in the overall transformation is the highly selective oxidative cleavage of enol ethers 3 with PCC under very mild reaction conditions.Application of this methodology has been exemplified in the synthesis of the Japanese beetle pheromone.
Substituent-directed oxidation: a simple preparation of γ and δ-lactones by oxidative cyclization of hydroxyalkenes.
Schlecht, Matthew F.,Kim, Ho-jin
, p. 127 - 130 (2007/10/02)
Treatment of tertiary γ- and δ-hydroxyalkenes with chromium trioxide in acetic acid/acetic anhydride gives reasonable yields of γ- and δ-lactones by oxidative cyclization, with loss of one carbon. A mechanism is proposed involving formation of a chromate monoester, followed by intramolecular oxidative attack on the alkene.
