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29.11.1.1.1.2 Variation 2: From Hydroxylamines

DOI: 10.1055/sos-SD-029-00649

Merino, P.Science of Synthesis, (200729709.

The reactivity of the hydroxy group of hydroxylamine is often very similar to that observed for a primary alcohol. Thus, the cyclic aromatic hydroxylamine 17 undergoes reaction with an excess of 2-methoxypropene in the presence of catalytic 4-toluenesulfonic acid to give, after 10 minutes, the NO protected hydroxylamine 18 (Scheme 7).[‌8‌]

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Meeeee 8 Meeeeeeee ee ee M-(Meeeeeeeeeeeeeeee)eeeeeeeeeeeee[‌8‌]

Me eee eeeeeee ee eeeeeeeee eeeeeeeeeee eee eeeeeeee eeeee 8 eeee ee ee ee eeeeeeeeee, eeeeeeee eeeeee eeeeee (8888%) eee eeeeeeee. Meeeeee eeeeeee eeeeeee ee eeeeeeeeeee ee eee eeeeeeee ee eee eeeeeee-eeeeeee eeeeeee 88, eeeeeeeee ee eeeeeeeeee eeee ee-eeee-eeeee eeeeeeee (Meeeee 8).[‌88‌] Mee eeeeeeee ee eeeeeeeeee eeeeeeeeeeee, eeee eeeeeee ee 88 eeeee eeeeee ee eeeee eeeeeee.

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Meeeee 88 Meeeeeeee ee e 8-(Meeeeeeeeeeeee)-8M-eeeeeee[‌88‌]

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8-(8,8-Meeeeeeee-8-{[(eeeeeeeeee-8M-eeeee-8-eeeee)eeeee]eeeeee}eeeeeee)eeeeeeee Meee (88):[‌88‌]

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Meeeeeee 88 (8.8e, 8.8eeee) eee eeeeeee eeee M-(eeeeeeeeee-8M-eeeee-8-ee)eeeeeeeeeeeee (8.88e, 88.8eeee) eee MM(MMe)8 (8eM) ee MMM (88eM) eee eee eeeeeee eee eeeeeee eee 8e ee ee eeeee M8. MeMM (88 μM) eee 8M MeMM8MM ee MMM (88.8eM, 88.8eeee) eeee eeeee ee eee eeeeeee, eeeee eee eeee eeeeeee ee ee eee 88e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMM/MeMM 88:8.8:8.88) ee eeee eee eeeeeee ee ee eee; eeeee: 8.88e (88%).

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