Über Umsetzungsprodukte von N‐(Diphenylmethylen)aminomethanol

Abstract

N-(Diphenylmethy1en)aminomethanol (2) wird iiber seine Lithiumverbindung 4 mit aliphatischen Saurechloriden, a-Halogenethern oder Chlortrimethylsilan in die Substitutionsprodukte 5,lO und 1 1 iibergefiihrt. Mit Nucleophilen wie Natriummethanolat, 2-Methyl-indandion-(1,3)-natrium oder Natriumcyanid reagiert das Acetoxyderivat 5a vermutlich iiber intermediar gebildetes 1,l-Diphenyl-2-azaalleniumkation unter N-0-, C-C-bzw. N-C-Verkniipfung zu 7, 8 bzw. 9. Reaction Products of N-(Diphenylmethylene)aminomethanolThe lithium compound 4 of N-(diphenylmethy1ene)aminomethanol (2) has been converted with aliphatic acid chlorides, a-haloethers and chloro(trimethy1)silane into the substitution products 5,lO and 11. With nucleophiles such as sodium methanolate, 2-methyl-l,3-indanedione-sodium or sodium cyanide the acetoxy derivative 5a reacts presumably via a 1 ,l-diphenyl-2-azaalIenium cation to yield 7, 8 or 9 with newly formed N-0, C-C and N-C bonds.

Product Class 7: Imines

“…Due to the lability of the N-hydroxymethyl group, the lithium salt has been derivatized with chlorotrimethylsilane, chloromethyl methyl ether, or acid chlorides. [393] On the other hand, direct N-alkylation of benzophenone imine can be performed by deprotonation with lithium diethylamide followed by reaction of the red-black anion with an alkyl halide or dimethyl sulfate. [394] The yield varies from 53 to 85%, except for the alkylation with allyl bromide, which only furnishes 17% of the desired imine.…”