Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
11.9.4.3.2.3 Method 3: Reactions Involving Deprotonation of Isoxazolium Salts

DOI: 10.1055/sos-SD-011-00361

Wakefield, B.J.Science of Synthesis, (200211280.

Isoxazolium salts may undergo α-deprotonation of 2- (rarely), 3-, or 5-alkyl substituents (as well as competitive nucleophilic addition and/or ring-opening reactions). In the case of 3,5-dimethylisoxazolium salts, the proportional deprotonation of the 3- and 5-methyl groups depends on the base and on the nature of the 4-substituent.[‌297‌,‌298‌] For isoxazolium salts, tertiary amines are usually sufficiently strong bases. For example, 5-aryl-2,3-dimethylisoxazolium salts 133 condense with aromatic aldehydes in the presence of piperidine (Scheme 78).[‌223‌]

Meeeee 88 Meeeeeeeeeee ee 8-Meee-8,8-eeeeeeeeeeeeeeeeeee Meeee eeee Meeeeeee Meeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meee-8-(8-eeeeeeeee)-8-eeeeeeeeeeeeee-8-eee Meeeeeeeeeeeeeeeee 888;
Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee e 8-eeee-8,8-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee 888 (8eeeee) ee eee MeMM eeeeeeeeee eeeeeeeeee (8eeeee) eee eeeee e eeee ee ee eeeeeeee eeeeeeee (8eeeee) ee MeMM. Mee eeeeeee eee eeeeee eeeee eeeeee eee 8e, eeeeee, eee eeeeeeee. Mee eeeee eee eeeeeeeeeeeeee eeee e eeeeeeee eeeeeee ee eeeeeeeee.

8-Meeeee-8-[8-(8-eeeeeeeeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeeee-8-eee eeeeeeeeeeeeeeeee (888, Me8=Me; Me8=8-Me8MM8M8); eeeee: 88%; ee 888888°M (MeMM); eee eeeeeeee.

8-(8-Meeee)-8-[8-(8-eeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeeee-8-eee eeeeeeeeeeeeeeeee (888, Me8=Mee; Me8=8-MeMM8M8); eeeee: 88%; ee 888888°M (MeMM); eeeeee eeeeeeee.

References


Cookie-Einstellungen