247216-13-3Relevant academic research and scientific papers
Preparation and Properties of 2-Methyleneoxetanes
Dollinger, Lisa M.,Ndakala, Albert J.,Hashemzadeh, Mehrnoosh,Wang, Gan,Wang, Ying,Martinez, Isamir,Arcari, Joel T.,Galluzzo, David J.,Howell, Amy R.,Rheingold, Arnold L.,Figuero, Joshua S.
, p. 7074 - 7080 (2007/10/03)
The methylenation of β-lactones 5 with dimethyltitanocene provides a versatile, reliable, and highly chemoselective entry to 2-methyleneoxetanes 7. The conversion proceeds selectively in the presence of alkenes, unprotected alcohols, and a variety of other carbonyl moieties. A study of conditions for the optimization of this reaction is delineated. In addition, the first X-ray structure of a 2-methyleneoxetane, which shows its similarity to related β-lactones, is reported. Reactivity studies of 2-methyleneoxetanes are presented in which it is demonstrated that these compounds are attacked at C-4 with a nucleophile; then, subsequently, the resultant enolate reacted with an electrophile. An interesting dichotomy of reactivity was observed when methyleneoxetane 7c was treated with electrophiles. Reaction of 7c with acetic acid gave acetoxyoxetane 19. When 7c was exposed to bromine, dibromoketone 20 resulted.
Oxoammonium salts. 6. 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1- oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis
Bobbitt, James M.
, p. 9367 - 9374 (2007/10/03)
4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate, 1, is a stable, nonhygroscopic oxoammonium salt that is easily prepared and can be used for the oxidation of alcohols to ketones or aldehydes in near quantitative yields. The reaction is colorimetric, does not require anhydrous conditions, does not involve heavy metals, and can be carried out conveniently. Furthermore, the oxidant can be easily regenerated. The oxidation is somewhat specific in that the relative reactivities of an allyl alcohol (geraniol), benzaldehyde, and 1-decanol are about 100:1:0.1. The reaction is catalyzed by silica gel.
