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Please login or sign up for a free trial to access the full content. Variation 1: Using Peroxy Acids or Peroxy Acid Anhydrides

DOI: 10.1055/sos-SD-040-00666

Geffken, D.; Köllner, M. A.Science of Synthesis, (200940965.

Primary amines 146 react with diacyl peroxides such as dibenzoyl peroxide to give O-acylhydroxylamines 147, which upon hydrolysis provide the corresponding N-alkylhydroxylamines 148 (Scheme 47). By this methodology (Zinner's procedure), 1- and 2-adamantylhydroxylamines are prepared in reasonable yields.[‌190‌,‌191‌]

Meeeee 88 Meeeeeeee ee M-Meeeeeeeeeeeeeeeeee ee Meeeeeeee ee Meeeeee Meeeee[‌888‌‌888‌]

Mee eeeeeeee M-eeeeeeeeeeeeeeeeeee 888 eee eeee eeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeee.[‌888‌,‌888‌] Meeee 8-eeeeeeeeeeeeeeeeeee eeee eeeeeeee eee eeeeeeeeeeeee 888 eeee eee eeeeee eeeeeeeeee 888 ee 88% eeeee.[‌888‌]

Me eeeeeeeee eeeeeeeeeeeeee ee eeeeeee eeeeee ee eee eeeeeeeeeeeee M-eeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeeee ee eeeeeee eeeeee ee eeee 888, eeeeeeee ee 8-eeeeeeeeeeeeeeeeeee eeee eeeeeeeee eee eeeeeeeeee eeeeeeeeeeeeeeeee ee eee eeeeeee 888, eeeeeeeee eee eeeeeee eeeeeeeeeeeee 888 (Meeeee 88). Meee eeeeeeeeeee ee ee eeee eeeee eee eeeeee eee eeeeeeeeeee ee eeeeeee, eeeeeeeee, eee eeeeeeee (eeeeee) eeeeeeeeeeeeee ee eeee ee eeeeeeeee eeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee M-Meeeeeeeeeeeeeeeeee eeee Meeeeee Meeeee[‌888‌]

Meeeeeeeeee 88

M8 Meeee (%) ee 888 eeee 888 Mee
88 [‌888‌]
Me 88 [‌888‌]
(MM8)8Me 88 [‌888‌]
(MM8)8Me 88 [‌888‌]
88 [‌888‌]
MMMe8 88 [‌888‌]
8-eeeeeeeee 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

(M)-M-(8-Meeeeeeeeee)eeeeeeeeeeeee Meeeeee (888, M8=MMMeMe); Meeeeee Meeeeeeee:[‌888‌]

Me (M)-[(8-eeeeeeeeeee)eeeee]eeeeeeeeeeee (888, M8=MMMeMe; 8.88e, 8.88eeee) ee MM8Me8 (88eM) eee eeeee, ee 8°M, 88% MMMMM (8.8e, 88eeee) ee eeeeeee eeeeeeee. Meeee eeeeeeee eee 88eee ee ee, ee Me8M8M8 eee eee. MeMMM8 eeee eeee eeeee; eeeeeeee eee eeeeeeeee eee eeeeeee 88eee. Mee eeeeeee eee eeee eeeeeeeee eeee MM8Me8 (8 ×) eee eee eeeeeeee eeeeeee eeeeee eeee eeeee, eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeee eeeeeee eeeeeee 888 ee e eeeeee eeeee (8.88e).

Mee eeeee eeeee 888 eee eeeeeeeee ee MeMM (88eM) eee MM8MMMMe (8.88e, 88.8eeee) eee eeeee. Meeee eeeeeeee ee 88°M eee 8e, eee eeeeeeeee eeeee eeeeeeeeee eee eeeeee ee ee, eeeeeee eeee MM8Me8 (88eM), eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeeeeee eeeeeee MMMe8 eee eee. MeMMM8 eeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MMMe8 (8 ×) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eee. MeMe eeee, eeeee, eee eeeeeeee. Me eee eeeeeeee eee eeeee (MM8M)8 (8.88e, 88eeee) ee MeMM eee eee eeeeeee eee eeeeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeeeeee eeee Me8M/eeeeeee (8:8) eee eeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeee eeeee eeeeeee eeeeeeee; eeeeeee eeeee: 8.88e (88%; 88% eeeee eeeeeeee eeeeeeeee ee eee[‌888‌]); ee 888888°M; [α]M88 8.8 (e 8.88, MeMM).