With sterically unhindered and certain moderately hindered α-chloronitroso compds. R1R2C(NO)Cl [R1 = R2 = Et; R1 = Me, R2 = Me2CHCH2, CH2Ph; R1R2 = (CH2)5], Me3Al at low temp. gives the methylnitrones R1R2C:N+MeO-. Several intermediate complexes lose methane upon heating and rearrange to α-chloroimines. More sterically hindered α-chloronitroso compds. contg. quaternary C undergo C-C rupture when treated with Me3Al, thus forming hydroxaminic acid chlorides, e.g., CH2:CMe(CH2)3CMe2CCl:NOH, formally HCl adducts of nitrile oxides. In the latter case, subsequent reactions lead to overall ring enlargement, i.e., formation of the seven-membered cyclic oxime I. With Et3Al and triisobutylaluminium, α-chloronitroso compds. are mainly reduced to oximes and the isomeric amides. [on SciFinder(R)]
|Number of pages||6|
|Journal||Recueil des Travaux Chimiques des Pays-Bas|
|Publication status||Published - 1986|
Bibliographical noteM1 - Copyright (C) 2018 American Chemical Society (ACS). All Rights Reserved.
CAPLUS AN 1987:83940(Journal)
- chloro nitroso reaction organoaluminum
- aluminum methyl reaction chloro nitroso