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18.2.4.1.13.1 Variation 1: Using Sodium Azide

DOI: 10.1055/sos-SD-018-00070

Braverman, S.; Cherkinsky, M.; Birsa, M. L.Science of Synthesis, (200518125.

The starting acyl azide 151 can be prepared either from carboxylic acid chlorides and sodium azide or by treatment of carboxylic acid hydrazides with nitrous acid. Otherwise, mixed anhydrides react with sodium azide under very mild conditions to form acid azides in excellent yields, which can be rearranged to isocyanates.[‌421‌]

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Meeeee 88 Meeeeeeee ee (Meeeeeeeeeeee)eeeeee eee (Meeeeeeeeeee)eeeeee Meeeeeeeeee[‌888‌]

M eeeee eeeeeee ee eeeeeeee eeeeeeeeeee eeee eeee eeeeeeee ee eeee eeeeeeee. Meee, eeeeeeeeeee 888 8-eeeeeeeeeee ee eee eeeeeee eeee eeee eee (eeeeeeeeeeeee)eeeeeeee eeeee eee eeeeee eeee eee eeeeeeeeeeeee eeee eeeeee ee eeeeeee eee 8 eeee ee 88°M ee 8,8-eeeeeeeeeeeeeee (Meeeee 88).[‌888‌] Meeeeeeee, M-eeeeeeeeeee 8-eeeeeeeeeeeeeeee eeeeee eeeeee eee eeeeeeeeeeeee 8-eeeeeeeeeeeeeee eeeeeeeeeee 888 (M8=8-MMMM8M8) eeee eeeeee ee eeeeeee eeeeeee.[‌888‌] Meeeeeeee eeeeee eeeeee eeeeeeeeeee eeeeeee ee eeeeeeeee eeeeee eeeee (e.e., 888, M8=MMMMMMMeMe),[‌888‌] eeeee (e.e., 888, M8=MM8MMMeM8; M8=eeeee),[‌888‌] ee eeeeee (e.e., 888, M8=MMMMeM8; M8=eeeee) eeeee[‌888‌] ee eee 8- ee 8-eeeeeeee ee eee eeeeee eeee eeee eeee eeeeeeeeeee eeee eeeeeeeeeeee eeeeeeee ee 88% ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeee eeeeee ee eeeeeee.

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Mee eeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee ee eeeeeeeeeee eeeeee eeeeeee eeeeeeeeeeee eeee eeee eeee eeeeeeeee ee eeeeeee eeeeeee eee eeeeeeeeeeeee eeee eeeeee.[‌888‌] Me eeeeeee, eeee e eeeeeee eeeeee ee eeeeeeeeeeee eeeeeeeeeee eeee eeee eeeeeeee eee eeeeeeeeeeeee ee eeeee eeeeeeeee eeee. Meee ee eeeee eeeeeeeeeee eeee eeee eeeeeeeee eee eeeeeee ee eeee eeee eeeeeeee ee eeeee eeeeeeeeeeee, eeeeeee eeeeee eeeeeee eeeeeeeeeee ee- eee eeeeeeeeeeeee eeeeee eeeee eeeeeeeeeee. Mee eeeeeeeeee eeeeeeee ee eeee eeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeee eeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeee. Me eeeee eeeeeeee eeeeeee eeeeeeeeeee, eeee 8-eeeeeee eeeeeeeeee (888) (Meeeee 88) eee eeee eeeeeeee ee eeee eeee ee e Meeeeee eeeeeeeeeeeee ee eeeeeeeeee eeeee ee eeeeeeeee eeeeeee, eeee eeeeeeeeeeee ee eeeeeeeeeeee ee 888888°M eeeee eee eeeeeeee.[‌888‌] Me eee eeeeeeee ee eeeeeeeeeee eeeeeeee, eeeeeeee 888 ee eeeeeee eeeeeeeee eeee e eeeeeeeeeeeee. Meeeeeeee, 8-eeeeee-8-eeeeeee eeeeeeeeee eee 8-eeeeee-8,8-eeeeeeee-8-eeeeeee eeeeeeeeee eeee eeee eeeeeeee ee Meeeeee eeeeeeeeeee ee eee eeeeeeeeeeeee eeee eeeeee ee eeeeeeeee eeeeeee.[‌888‌] Mee eeee eeeeeeee eee eeee eeee eee eee eeeeeeeeeee ee eeeee eeeeeeeeeeee eeeeeeeeeee, eeee ee eeeeeeeeee eeeeeeeeeee ee eeeeee (e.e., 888, M8=M), 8,8-eeeeeeeeeeeeee (e.e., 888, M8=Me; 888),[‌888‌] e-eeeeeeee (e.e., 888),[‌888‌] eee eeeeeeee (e.e., 888, 888).[‌888‌]

Meeeee 88 Meeeeeeeeeee Meeeeeeeeee eeee Meeeeee Meeeeeeeeeeee[‌888‌‌888‌]

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Meeeee 88 Meeeeeeee ee Meeee Meeeeeeeeee[‌888‌]

Meeeeeeeee eeeeeeeeeee eeeeee e eeeeeeeee ee eeeeee[8,8-e]eeeeeee eeee eeeee ee eee eeeeee eeeee eeeeeee eee eeee eeeeeeee (e.e., 888, 888) eee eeeeeeeeeeee eeeeeeee ee eeeee eeeeeee ee eee eeeeeeeeeeeee eeeeee ee e Meeeee eeeee eee eeeee ee eeeee 888888°M (Meeeee 88).[‌888‌,‌888‌] Meeee eeeeeeeeeee ee eee eeeee eeeee eee eeeeee eeeeeeeee, eeeeeeee eeeeeee ee eeeeee eeeeeeee, eee eeee eeeeeee eeeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeee.

Meeeee 88 (Meeeeee)eeeeee Meeeeeeeeee[‌888‌,‌888‌]

Meeee eeeeeeeeeee eee eeeeee eeeeeeee ee eeeee eee Meeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeee eeeeee, eeeeeee eeeeeeee eeee α,β-eeeeeeeeeee eeeee. Meeeeee, eeee eee eee eeeeeeee, eee eeee ee eeeeeee eeeeeeeee eee eeeeeee eeeeeeeeeeeeeee. Mee eeeeeee, eee eeeee eeeeeeee eee eeee eeeeeee ee eee eeeeeeeee ee eeeee (8M)- eee (8M)-8-eeeeee-8-[(eeeeeeeeeeee)eeeee]eeeeeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeeeeeeeeee eeeee eeeeeeeeee 888 ee eeee eeeeeeeee ee ee eeeeeeeeeeeee 8:8 eeeeeee ee M- eee M-eeeeeee ee eeeeee e eeeeeee eeeeeeee ee eeee eeeee 888 ee eee eeeeeee (888°M) eee eeeeeee eeeeeee eee eeeeeeee ee 8°M. Mee eeeeeeeeee 888 ee eeeeee ee eeeeeeee eee eeeeeee eeee; eeeeeee, eeeeeeee ee e eeeee eeeeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeee-8-eee eeeeeee eeeeeeeeee ee.

Meeeee 88 Meeeeeeee ee Meeee (8M)- eee (8M)-8-Meeeee-8-[(eeeeeeeeeeee)eeeee]eeeeeeeee[‌888‌]

Meeeeeee-8-eeee eeeeeeeeee (888), eeeeeeee eeee eeeeeeee-8-eee-8-eeeeeeeeee eeee, eee eeeeeee eeee ee eeeeeeeeeee eeeee eeeeeee ee 8°M eee eeeeeeee ee eeee eeeee eee eeeeee 888. Mee eeeeee, eeee eeeeee eee e eeeee eeeeee (888eee) ee 888888°M, eeeeeeeee eeeeee eeeeeeeeeee ee eeeeeee eee eeeeeeeeeeeee eeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee eee Meeeeeeeeee ee Meeeeeee-8-eeee Meeeeeeeee[‌888‌]

Me eee eeeee eeeeeeeeeee, eeeee eeeeeeeeeee 888, eeeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeeeee eeee eeeeee 888, eee eeeeeee eeee eeeeeeeeeeeeee eeeeeeee ee eeeeee eee eeeeeeee 888 (Meeeee 88).[‌888‌,‌888‌] Meeeeeee eeee eeee (M)- eee (M)-eeeeeeee eeeee, eeee eee M-eeeeee 888 (M8=Me) eee eeee eeeeeeee eeeee ee eeeee eeeeeeeeee eeeeeeeeeeeee.[‌888‌] Meeeeee, ee ee eeeeeeee eeee eeeeeeeeeeeee eeeeeeee ee eee eeeeeeeee eeee. Meee, eeee e eeeeeee ee M- eee M-eeee eeeeee 888 [M8=(MM8)8MMe] eeeeeeee eeee (8M)-8-(eeeeeeeee)eeee-8-eeeee eeee, ee eeeeeeeee ee eeeeee eee eeeeeeeeeeeeee, eeee (M)-eeee eeeee 888 eeeeeeeee eeeeeee eeeeeeeeeeeee ee eeeeeee; ee eeeeeeee ee eee eeeeeeeee eeeee eeeeeeeeee 888 ee e eeeeeeee ee eeeeeeeeeeeee ee eeeeeeeeeeeeeee ee 88°M, eee eeeeeee (M)-eeeeeee 888 [M8=(MM8)8MMe; M8=Me] ee eeeeeeee ee 88% eeeee eeee eeee eeeeeeeee ee eeeeeeeeeeeee.[‌888‌]

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Meeeeeee eeeeeeeeeee eee eeee ee eeeeeeeeeeee eeeeeeee eeeeeeeee eee eeeee eeeeeeee. Meee, α-eeeeee eeeeeeeeee 888, eeeeeeee ee eeee ee eeeeeeeeeee ee eee eeeeeeeeeeeee eeee eeeee, eee eeee ee eee eee eeeeeeeeeeee ee eee eeeeeeeee ee 8-eeeeeeeeee[8.8.8]eeeeee-8-eee (Meeeee 88).[‌888‌] Meeeeee eeeee-eeeeeeeeeee eeeeeeeeee eeee eeeeee ee eeeeeeeee eeeeeee eeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeee 888 ee eeeeeeeeeeee eeeee, eeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeee Meeeeeeeeee ee Meeeeee Meeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee ee eee Meeeeee eeeeeeeeeeeee ee eeeee eeee eeeeeeeeeee eee eeee eeeeeeeee. Meee, eeeeeeeeeeeeee ee M-eeeeeeee eeeee eeee eeeeeeeeee ee eee eeeeeeeeeeeee M-eeee-α-eeeeeeeeee eeeeeeeeeee 888, eeeee eee eeeeeeeeeeee eeeeeee eeee ee eeeeeee ee eeeeee eee eeeeeeeeeeeee eee-eeeeeee eeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee eee Meeeeeeeeee ee M-Meee-α-eeeeeeeeee Meeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-(8,8-Meeeeeeeeeeeeeeee)-8M-eeeeeeeee-8,8(8M)-eeeee (888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

M eeeeeeeeee ee 8-(8,8-eeeee-8,8-eeeeeeeeeeeeeee-8-ee)eeeeeeee eeee (8.88e, 8.88eee) ee MMM/M8M (88eM) eee eeeeeee ee 8°M eee e eeee ee Me8M (8.88e, 8.888eee) ee MMM (8eM) eee eeeee eeeeeeee eeee 88eee. Meeee eeeeeeeeeeeee (8.88e, 8.888eee) eee eeeee eeeeeeee eeee 88eee ee eee eeeee eeee eeee eeeeee eee eeeeeeee eee eeeeeeeee eee eeeeeee 88eee. M MeM8 (8.888eee) eeee ee M8M (88eM) eee eeeee eeeeeeee eeee 88eee, eee eeee eee eeeeeee eee eeeeeee eee 8e ee 8°M, Meee, M8M (888eM) eee eeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee eeeeeee ee eeeeee ee. Mee eeeeeeeee eee eee eeeeeeeee eeee eeeeeee (MMMMMMM: eeeeeeeeee) eee eeeee (Me8MM8). Mee eeeee eeeeeee eeeeeee eee eeeeeeee eee 88e. Meeeeeeeeee ee eee eeeeeee eee eeeeeeeeeeeeeeeee (eeeeeee/MMM) eeeeeeee ee eee eeeeeeeeeeee; eeeee: 8.88e (88%); MM (MMe) ν̃eee: 8888ee8 (MMM).

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