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Please login to access the full content or check if you have access via Variation 2: N-Alkylation by Ritter-Type Reactions

DOI: 10.1055/sos-SD-021-00021

Ziegler, T.Science of Synthesis, (20052161.

Montmorillonite KSF clay under microwave irradiation catalyzes the Ritter reaction of a wide variety of primary, secondary, and tertiary alcohols with nitriles to afford the corresponding amides 17 in 75% yield (Scheme 29).[‌96‌] Similarly, Nafion-H resin can be used for the same purpose.[‌97‌]

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Meeeeeeeeee 88

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M M 8-MeMM8M8 Me 8 88 [‌88‌]
M Me Me MM=MM8 8 88 [‌88‌]
M M 8-MeMM8M8 Me 8 88 [‌88‌]
M Me Me e-Me 8 88 [‌88‌]
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Meeeeeee M-eeee-eeeee eeeeee 88 eee eeeeeeee eeee eeeeeeee eeeeeeee eee eeee-eeeee eeeeeee eeee eeeeeeee eeee ee 8888% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeee Meeeeeee ee Meeeeeee Meeeeeee eeee eeee-Meeee Meeeeee[‌88‌]

Meeeeeee eeeee eeee eeeee eeeeeeeeeeeeee eee eeeeeeee(M) eeeeeeee ee eeee eeee eeeeee ee M-eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeee 88 eeeee eeeeee eeeeee 88 eeee eeeeeeeeee (Meeeee 88).[‌88‌] Mee eeeeeeeee eee eeeeeee eeee eee eeeeeeeeeeeee ee eeeee ee eeeeeeeeeeeee, ee eeee eeee eeeeee eee eeeee eeeeeeeeeeeeee eee eeeeeee M-eeeeeeeeeeeeee eeeee eeeeeeee.

Meeeee 88 Meeeee Meeeeeee ee Meeeeeee eee Meeee Meeeeeeeeeeeee eeee Meeeeeee(M) Meeeeeee[‌88‌]

Meeeeeeee, Meeeee eeeeeeeee ee eeeeeeee eee eeeeeeee eee eeeeeeeee ee eeeeee eee eeeeeeeee eeee(MMM) eeeeeeeeeee[‌888‌] ee eeee(MMM) eeeeeeee eeeeeeeeeee,[‌888‌] eeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee,[‌888‌] eee eeeeeee eeeeee Meøeeeee eeeee eeee ee eeeeeeee eeee, eeeeeeeeeeeeee eeee, eeeeeeeeeeeeee eeee, eee eeeeeeeeeeeeeee eeee.[‌888‌]

Meeeeeeeeeeeee eeeeee 88 eee eeeeeeee eeee eeeeeeee eee eeeeeeeeeeeeeeee ee eeeeeeeee eeee ee e eeeeeeee ee eeeeee eeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeee Meeeeeee ee Meeeeeeeeeeeeeee ee Meeeee Meee[‌888‌]

Meeeeee eeeee eeee eeeeeeeeeeee eee (eeeeeeeeeeeeeee)eeeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeeeeeeeee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeeeee Meeeee eeee Meeeeee eee Meeeeeee[‌888‌]

Meeeeeeeee 88 eee eeeeeeee eeee eeeeeeeee ee eeeeeeee eeeeeeee, eeeeeeeeeeeeee eeeeeee, eee eeeeeeee eeee ee eeee eeeee (Meeeee 88). Meeeeee eeeeeeee ee eee eeee eeee Meeeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeee Meeeeeee ee Meeeeeee eee Meeeeeeeeeeeee Meeeeee[‌888‌]

Meeeeeeeeeeeee eeeeee eeee eeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeee eeeee M-eeeeeeeeeeeeeeeeee eeee eeeeeeee eeeeee(MM) eeeeeee.[‌888‌]

Meee-8-eeee eeeeeeeeee eeeee eeee M-eeeeeeeeeeeeeeee eee eeeeeeeeeeee ee eeee ee eeeeeeeeeeee eeeeeeee eeeeeeeee eeee 88 eeeee ee eeeeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eeeeeeeee ee eeeeeeeee eeee ee eeeeee eeeeeeeee eeee eeeeeeee eeee e eeeeeeeeee eeee (Meeeee 88). Mee eeeeee eeeeee eeeeeeeee eeee eeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeeee.[‌888‌]

Meeeee 88 Meeeee Meeeeeee ee Meee-8-eeee Meeeeeeeee[‌888‌]

8-Meeee-8-eeeeeeeeeeeeeeeeeee eeeeeeeeee eeee ee 88 eeeee eeee eeeeeeee eee eeeeee eeeee ee eeeeee M-(8-eeeee-e-eeeeeeee) eeeeee (Meeeee 88).[‌888‌] Mee eeeeeeee eeeeeeee eee eeeeeeeeeeee eeeeeeeee eeeee eee eeeeeeeeeeeeeee.

Meeeee 88 Meeeee Meeeeeee ee 8-Meeee-8-eeeeeeeeeeeeeeeeeee Meeeeeeeee[‌888‌]

Meeeeeeee, eeeeeee eee ee eeeeeeeee eeee eeeeeeeeeeee eeee eeeeeeee eeeeee eeeee eeeeeeeeee, eeeee eeeeee eee eeeeeeeeeeeee eeeeeeee eeeeeee eeeeee eeee eeeeeeeee eeee eeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeee Meeeeeee ee Meeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee 88 ee Meeeee Meeeeeee ee Meeeeeee eeee Meeeeeee Meeeeeeee ee Meeeeeeeeeeeeee MMM Meee eeeee Meeeeeeee Meeeeeeeeee; Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeee (88eeee) eee eee eeeeeee (88eeee) eeee eeeeeee eeee eeeeeeeeeeeeeee MMM eeee (8.8e) eee eeeeeeeee ee eeeeeeeee eeeeeeeeeee ee e Meeee eeee eeee eee 88eee. Mee eeeeeeee eeee eee eeeeee ee ee, eeeeeee ee e eeeee eeeeee eee eeeeee, eee eeeeee (MeMMe/eeeeee 8:8) ee eeeeee eee eeee eeeee.

8-Meeeeee-M-eeee-eeeeeeeeeeeeee (88, M8=8-MMe); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee eeee ee 8-eeeeeeeeeeeeeeeeeee (88.8e, 888eeee) ee e-MeMMe (88.8eM) ee e 888-eM, eeeee-eeeeee, eeeee-eeeeeeee eeeee eeeeeeee eeee eeeeeeeee, eeeeeeeeeee eeeee, eee eeeeeeee eeeeee eee eeeee eeeee M8MM8 (8.8eM) eeeeee ee ee eeee eeeee 8eee. Mee eeeeeeeee eeee eee eeeeeee ee ~88°M eee ~8e ee eeeeeeee eee eeeeeeee. Mee eeeeeee eee eeeeee eeee eeee 88% ee MMMM8 (888eM) ee eeeeeeeeee eee eeee eee eeeeeeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee eeee M8M, eee eeeee eeeee eeeeee.

Meeeeeeee Meeeeeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee MeMe8 (8.88e, 88eeee) ee MM8Me8 (8eM) eee eeeee eeeeeeee ee e eeee (88°M) eeee ee eee eeeeeee (88eeee) ee MM8Me8 (8eM). M eeeeeee eeeeeee eeeeeeeeeeee. Mee eeeeeeeeee eee eeeeeee ee 88°M eee 88eee. Meee, ee 88°M e eeee ee eee eeeeeeeeeeeee (88eeee) ee MM8Me8 (88eM) eee eeeee eeeeeeee. Mee eeeeeee eee eeeeeee ee e eeeeeeeeeee eeeeeee 88 eee 88°M eee 88888eee, eeeeeeeee ee eee eeeeeeeee. Meeeeee (88eM) eee eeeee eeeeeeee eee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee e eeeee eeeeee ee MM8Me8.

Meeeee 88 ee Meeeeeeeee ee Meeeeeeee Meeee; Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeeeee eeee (88eeee) eee eeeeeee ee e eeee ee MeMM (8.88e, 88eeee) ee M8M (88eM) ee 88°M eee 88eee eee eeee ee 88°M eee 88eee. Meeeeeee eeeeeeeeee eeee Me8M eee eeeee eeeeee eeeeeeee eee eeeee, eeeee eee eeeeeeee eeeeee ee eeeee eeeeeeeeeeeeee [eeeeee eee (88e), MeMM/MM8Me8] eee/ee ee eeeeeeeeeeeeeee ee 88°M (MM8Me8/eeeeee ee eeeeee).

Meeeeeeeeeeeee Meeeee 88; Meeeeee Meeeeeeee:[‌888‌]

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Meeeeeeeee 88 eee Meeeee Meeeeeee; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee ee eee eeeeeee (88eeee) eee MMMMM (88eeee), eeeeee ee 88°M ee ee eee/eeee eeee, eeeee M8, eee eeeee eeeee M8MM8 (88eeee) eeeeeeee eeee eeeeeeee eeeeeeee (MMMMMMM: eeeeee eeeeeeeeee). Meeee eee eeeeeeee, eee eeee eeee eee eeeeeee eee eee eeeeeee eee eeeeeee ee eeeeeee eeeeeeeeeee eee 88e. Mee eeeeeee eee eeee eeeeee eeee eee, eee eeeeeeeeeee eeee 88% MeMM eeee ee eM ~8. Mee eeeeeee eeeee eee eeeeeeeee eeee e-MeMMe ee MMMe8, eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee eee eeeee (MeMM8). Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee (eeeee) ee eeeee eeeeeeeeeeeeee (eee).