6632-94-6

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InChI:InChI=1/C11H24O/c1-4-7-10-11(12,8-5-2)9-6-3/h12H,4-10H2,1-3H3

Upstream product

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• 41329-93-5 2,2-dipropyl-1,3-dioxolane 
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Relevant academic research and scientific papers

Approaches to primary tert-alkyl amines as building blocks

Primary tert-alkyl amines include analogues of amantadine, a fragment commonly linked to pharmacophoric groups to enhance biological activity. The preparation of primary tert-alkyl amines is considered to be a difficult problem. Four synthetic procedures, some of which have been previously reported for the synthesis of amines with primary (RCH2NH2) or secondary (RR'CHNH2) alkyl and/or aryl groups, were tested for the synthesis of primary tert-alkyl amines (RR′R″CNH2) in aliphatic series including adamantane adducts. These procedures included the formation and reduction of tert-alkyl azides, the Ritter reaction in standard and modified conditions, the addition of organometallic reagents to N-tert-butyl sulfinyl ketimines and one-pot reactions between nitriles and organometallic reagents in the presence of a Lewis acid, Τi(iPrO)4 or CeCl3. These synthetic routes are unexplored for primary tert-alkyl amines. Studies on the synthetic routes for primary tert-alkyl amines are currently lacking. The reaction conditions and substrate limitations were studied for each procedure, with the first procedure being the most general and applicable also for compounds bearing bulky adducts.

Salt effects on the reactivity and the stability of organomanganese reagents

The reactivity and the stability of organomanganese reagents prepared from the ate complexes MnX2·2LiBr (X= Br,I) and MnCl2·R4NX (X= Br, Cl) were studied. The preparation and the use for synthetic applications of stable sec- and tert-alkylmanganese bromides in ether as well as the acylation of RMnCl by R'COOCOOEt in THF were successfully achieved for the first time.

ORGANOMANGANESE (II) REAGENTS XII1: AN EFFICIENT ONE-POT PREPARATION OF UNSYMMETRICAL SECONDARY OR TERTIARY ALCOHOLS

Various unsymmetrical secondary or tertiary alcohols have been prepared in high yields by an efficient one-pot procedure involving the acylation of an organomanganese reagent by an acyl chloride and the addition to the ketone formed of various organometallic compounds (RLi, RMgX, LiAlH4, NaBH4).The complexation of the intermediate ketone by the metallic salts present in the reaction mixture allows to perform the 1-2 addition step under exceptionally mild conditions ( to 20 deg C).

REACTION OF ETHYLENEACETALS WITH RLi-TMEDA COMPLEXES

Tertiary alcohols are formed on treatment of 2,2-disubstituted 1,3-dioxolanes with RLi-TMEDA complexes.