ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Lithium- and copper-derivatives of α,α-doubly deprotonated nitroalkanes. Generation, properties and reactions with alkyl- and allylhalidesAus der Dissertation von F.L., ETH Zürich, 1979; Nr. 6356. Die Arbeiten wurden teilweise am Institut für Organische Chemie der Justus-Liebig-Universität Giessen durchgeführt. Vorläufige Mitteilungen siehe [1] und [2].Primary nitroalkanes are deprotonated twice in the α-position when treated with two mol-equiv. of butyllithium at -78° to -100° in THF containing HMPT to give dilithium derivatives 15 (the compound with R = C2H5 is stable up to -30°). The acidity of the nitronate proton of 13 is estimated to be in the same range as that of diisopropylamine. The C-nucleophilicity of the novel reagents 15 is dramatically increased as compared with that of simple nitronates 5: C,C-bond-forming reactions readily take place with alkylhalides (→22c-e,g,h,j-m) and benzylbromide (→22b,f,i); allylations are possible via nitroalkycopper-lithium-derivatives (→27-29).
Additional Material:
6 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19790620721