- Azodicarbonyl dimorpholide (ADDM): An effective, versatile, and water-soluble Mitsunobu reagent
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One of the caveats of the Mitsunobu reaction is the often difficult and laborious purification of the reaction mixture. Herein, we show that azodicarbonyl dimorpholide (ADDM) is an effective and versatile Mitsunobu reagent, which, along with its reduced form ADDM-H2, may be removed from the reaction mixture by a simple aqueous extraction. Furthermore, we demonstrate that the isolated ADDM-H2 may be re-oxidized with silver(I) oxide to regenerate ADDM. Finally, a chromatography-free Mitsunobu reaction is presented.
- Lanning, Maryanna E.,Fletcher, Steven
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p. 4624 - 4628
(2013/08/23)
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- Base catalyzed Mitsunobu reactions as a tool for the synthesis of aryl sec-alkyl ethers
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A facile and versatile method for the synthesis of aryl sec-alkyl ethers from phenols with alcohols in the presence of base via a Mitsunobu reaction is described.
- Manivel, Pitchai,Rai, Neithnadka Premsai,Jayashankara, Vaderapura Puttaramegowda,Arunachalam, Pirama Nayagam
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p. 2701 - 2705
(2008/02/03)
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- Reactions of 1-(α-Alkoxyalkyl)- and 1-(α-(Aryloxy)alkyl)benzotriazoles with the Grignard Reagents. A New and Versatile Method for the Preparation of Ethers
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1-(α-Alkoxyalkyl)benzotriazoles deriving from aldehydes (other than formaldehyde), or from ketones, react with Grignard reagents at 110 deg C to provide a high-yielding, general synthesis of dialkyl and aryl ethers.Under similar conditions, 1-(alkoxymethyl)- and 1-((aryloxy)methyl)benzotriazoles give, by a different cleavage pattern of the N-C-O grouping, 1-alkylbenzotriazoles and N,N'-dialkyl-o-phenylenediamines.The 1-(α-alkoxyalkyl)benzotriazoles are easily prepared: (a) by condensation of benzotriazole, an aldehyde, and an alcohol under water-removing conditions; (b) by condensation of a 1-(α-chloroalkyl)benzotriazole with a sodium or potassium alkoxide or aryloxide; and (c) by condensatioon of an acetal or a ketal with benzotriazole.All the 1-(α-alkoxyalkyl)benzotriazoles and dialkyl or alkyl aryl ethers obtained were fully characterized by their 1H and 13C NMR spectra.
- Katritzky, Alan R.,Rachwal, Stanislaw,Rachwal, Bogumila
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p. 6022 - 6029
(2007/10/02)
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