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
21.1.5.3.1 Variation 1: From Ketones with Alkyl Azides

DOI: 10.1055/sos-SD-021-00115

Judd, W. R.; Katz, C. E.; Aubé, J.Science of Synthesis, (200521150.

Attempts to form the corresponding N-alkyl amides by reactions of alkyl azides under standard Schmidt conditions fail.[‌37‌,‌50‌] A notable exception is the reaction of aromatic aldehydes with alkyl azides, although this reaction occurs in only a very small number of cases to give modest product yields.[‌51‌] The use of Lewis acid activation instead of the protic conditions used in the standard Schmidt reaction permits a wider variety of alkyl azide mediated Schmidt reactions of a broader, but still limited, range of cyclic ketones (e.g., 49); an example is given in Scheme 22.[‌52‌,‌53‌]

Mee eeeeeeee eeeeeeee Meeee eeee eeeeeeeeee ee eee eeeeeeee eeeee, eeeeeeee ee eeeeeeeeeeee eeeeee ee eee eeeee eeeee ee eeeeee e eeeeeeeeeee eeeeee, eeeeeee ee eeee eeeeeeee ee eee Meeeeee eeeeeeee ee eeeeeeeee eeee. Me eee Meeeeee eeeeeeee ee eeeeeeeee eeee, eeeeeeeeeee eeeee eeeeee (eee Meeeee 88, Meeeeee 88.8.8.8), eee eee eeeee eeeee/eeeeeeee eeeeee eee eeee eeeeeee eeeeee eeeeeeeee ee eeeeee eee eeeeeee.

Meeeeeee(MM) eeeeeeee (8.8 eeeee) ee eeeeeeeeeeeeeee ee eee eeee eeeeeee eee eeeeeeeee eee eeeeeeeeeeeeee Meeeeee eeeeeeee eeeeeee eeeeee eeeeeee eee eeeee eeeeee.[‌88‌] Me eeee eeeee, eeee eeeee eeeeeeeee eeeeeee ee eeeeee eee eeeee, e eeeeeeeeeee eeeeee ee ee eeeee eeeeeeee eeeeeeeee eeee eee eeee-eeeeeeeeeeee ee eee eeeeee ee eeeeeeee. Meee eeeeeeeee eeeeeee eee ee eeeeeeeee ee eee eee ee eeeeee eeeee.

Meeeee 88 Meeee Meee Meeeeeee Meeeeeeeeeeeee Meeeeee Meeeeeee eeee ee Meeee Meeee[‌88‌,‌88‌]

Me eeeeeee, eeeeeeeeee eeeeeeeeee eeeeeee, eeeeeeeeee eeeeeeeeeeeeee (e.e., 88), eee eee eeee eeeeeeeeee eee eeee eeeeeeeeeeeeee (e.e., ee eeee 88) (Meeee 8); eeeeeee, eeee eeeeee α-eeeeeeeeeeee eee eeee ee eeeeeeee eeeee eeeeee eee eeeeeeee eeeeeeeee. Meeeeeee, eeee eeeeeeeeeeeeeeeeee eee eeeee eeeeeeee (eeeee 8). Meeeeeeeeeeeeee eee eee eeee Meeeeee eeeeeeee eeeeeeee eee eeeee eeeeee (eeeee 8). Meeeeeeee eeeee eeeeee eee eeeeeeeee eee eeee eeeee eeeeeeeee eee eeeeeeeee eeeeee eeeeeeeee. Mee eee ee eeeeee eeeee eee, eeeee eeeeeee eeeeeeeeeeeee, eeeeee ee eeeeeeeeeee eeeeeee ee Meeeeee-eeee eeeeeeeeee, eeeeee eeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeee eeee ee eeee ee eeeeeee eee eeeeeeee (eeeee 8).[‌88‌]

Meeee 8 Meeeeeeeeeee ee Meeee ee eee Meeeeeeeeeeeee Meeeeee Meeeeeee ee Meeee Meeeee eeee Meeeeee[‌88‌]

Meeee Meeeee Meeee Meeeeeeeee Meeeeee(e) Meeee (%) Mee
8 Me(MM8)8M8 MeMe8/MM8Me8 88 [‌88‌]
8 MeM8 MeMe8/MM8Me8 88 [‌88‌]
8 Me(MM8)8M8 MeMe8/MM8Me8 + 8, 88 [‌88‌]
8 Me(MM8)8M8 MeMe8/MM8Me8 88 [‌88‌]
8 Me(MM8)8M8 MeMe8/MM8Me8 <8 [‌88‌]
8 MeM8 MeMM 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: MeMe8 eeeeee eeeeeeeee eeee eeeee, eeeeee eeeee, eee ee eeeeeeeeee ee eee eeee eee eeeeeeeeeee eeeeee. Mee eeeeeeeee eeeee eeee eeeeeee eeeeee ee eeeeeeeee ee e eeee-eeeeeeeeee eeee eeee eeeee eeeeeeeee eeeeeeeeeee eeeeee eeeeeeeeeee.

MeMe8 (8.8 eeeee) eee eeeee eeeeeeee ee 8°M ee e eeee ee eeeeeeeeeeeee (88; 8.8 eeeee) eee 8-eeeeeeeeeee (8.8 eeeee) ee MM8Me8; ee eeeeeeeeee eeeeeeee eeeeeeee eeee eee eeeeeeeee ee eee. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeee eee ~88e. Me eee eeee eeeeeee eeee MeMMe eee eeeeeeeeeee eeeeeee MeMMe eee eee. ee MeMMM8. Mee eeeeeee eeeee eee eeeeee eeee eeeee eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeee ee eeeeeeeeeee ee eee eeeeeee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 88%.

References


Cookie-Einstellungen