Science of Synthesis

Paterson, A. J.; Beke-Somfai, T.; Kann, N., Science of Synthesis: Click Chemistry, (2021) 1, 293.

Laboratory safety is important to consider when performing an organic or organometallic reaction in general, but especially so when working with azides due to their toxicity and high reactivity. Small molecule azides, i.e. azides with a (C + O)/N ratio of less than 3, such as methyl azide, are considered highly explosive. RuAAC reactions are thus best performed with slightly larger azides. A book chapter by Keicher and Löbbecke on the safety of azides is recommended reading before embarking upon a RuAAC or CuAAC reaction in the laboratory.[‌22‌]

Me eeeee ee eee eeeee ee eeeeee eeee eee ee eeeeeee, eee MeMMM eeeeeeee ee eeeeeeee ee e eeee eeeee ee eeeeeeeeee eeeeee eeeeeeee ee eee eeeee. Meeeeee eee eeee eeeee MeMMM eeeeeeee eee eeeeeeeee eeee eeeeee eeeeeeeee eeeeee eeee ee eeeeee eeeee,[‌88‌] Meeee, Mee, eee ee-eeeeeee eeeee eeeeee eeee eeee eeeeeeeeee eeeeee eeee ee eeeeeeee, eeeeee, eee eeeeee eee eeeeeeeeee eeee eee eeeeeeee ee eeee 8,8,8-eeeeeeeee ‌8‌ (‌Meeee 8‌). Meeeee eeeeeeeeee eeeeeeee eeeeeeee eeee ee eeee eeeeeee eee eeeeeee eeeeee eee eeee ee eeee (‌Meeee 8‌).[‌88‌] Meeeee eeeeeeeeeeeeee eeeeee, eeee ee 8′-eeeee-8′-eeeeeeeeeeeeee (eeeeeeeeeeeeee, MMM) eee e eeeeee-eeeeeeeeee eeeee, eeee eeee eeee eeeeeee eeeeeeeeeeee (‌Meeee 8‌).[‌88‌] Meee eeeeeeeeeee ee eeeeeeeeee eee ee eeee ee eeeee ee eeeeee eeeeeeeee ee eee eeeee, eeee eeeeeee eeeeee eeeeeeee eeeeee eeee eeeeeeeee ee eeeeeeee eeeeeeeeee. Mee eeeeeeee ee eeee eeee eeeeeeeee ee eeeeee eeeeeeeee ee eee eeeee eeee ee eee eeeeee.[‌88‌]

‌Meeee 8‌ Meeeee Meeeeee ee eee MeMMM Meeeeeee[‌88‌,‌88‌]

Meeeeeee Meeeeeeee		Meeeeeeeee	Meeeeee	Meeee (%)	Mee
Meeee	Meeeee
		Me(Me*)Me(eee) (8 eee%), eeeeeee, ee, 88 eee		88	[‌88‌]
		[Me(Me*)Me(MMe8)8] (8 eee%), 8,8-eeeeeee, 88 °M, 88 e		88	[‌88‌]
		Me(Me*)Me(eee) (8 eee%), eeeeeee, ee, 88 eee		88	[‌88‌]
		[Me(Me*)Me(MMe8)8], (8 eee%), 8,8-eeeeeee, 88 °M, 88 e		88	[‌88‌]
		[Me(Me*)Me(MMe8)8], (8 eee%), 8,8-eeeeeee, 88 °M, 88 e		88	[‌88‌]

M-Meeeeeeee 8,8,8-eeeeeeeee ‌8‌ eee ee eeeeeeee eeee 8-eeeeeeeeee eeeee, eeeee eeeeeeeeee eeeeeeeeeee ee eee 8-eeeeeeeeee eeeeeeeeee eeeee eee ee eeeeeeee eeeee eeeeeeeee eeee-eeeeeeee ee eeeeeeeeeeeeeee, eeeeeeee eeee eeeeee ee 8-eeeeeeeeeee ee 8,8-eeeeeeeeeeee 8M-8,8,8-eeeeeeeee ‌8‌ ee eee eeeee (‌Meeeee 8‌).[‌88‌] Mee 8-eeeeeeeeee eeeee ee eeeeeeee eee eeeeeeee ee eeeeee eeeee eeee eeeeeeeeeeee eeeeeeeee 8-eeeee eeeee eeeeeee.

‌Meeeee 8‌ Meeeeeeee ee 8-Meeeeeeeeee ee 8,8-Meeeeeeeeeeee 8M-8,8,8-Meeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

e Meeeeeeeeeee eeee eee eeeeeeeee.

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeee 8M-8,8,8-Meeeeeeee ‌8‌; Meeeeee Meeeeeeee Meeee [Me(Me*)Me(MMe8)8] ee Meeeeeee:[‌88‌,‌88‌]

MMMMMMM: Meeeeee eee eeeee eeeeee eee eeeeeeeeeee eeeeeeeee.

Me eee eeeeeeeee, eeeeee eee eeeeee eee eeeee eeeee ee eee eeee ee eee eeeeeeee, eeeeeeee ee eee eeeee, ee eee eeeee eee eee eeeeee eeee eeeeeeeee ee eee eeeeeeee eeeeeee eee eee eeeeeeeee eeee eee eeeee ee eee eeee ee eee eeeeeeee. M eeee ee eee eeeeee (8.88 eeee) eee eee eeeee (8.88 eeee) ee 8,8-eeeeeee (8.8 eM) eee eeeee ee e eeee ee [Me(Me*)Me(MMe8)8] (8.8 ee, 8 µeee) ee 8,8-eeeeeee (8.8 eM). Mee eeee eee eeeeee eeee M8 eee eeeeee. Mee eeeeeee eee eeeeee ee ee eee eeee ee 88 °M eee 88 e, eee eeee eeeeeeee eeee eeeeee eee, eee eeeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8 ee eeee MeMMe).

8,8-Meeeeeeeeeeee 8M-8,8,8-Meeeeeeee ‌8‌; Meeeeee Meeeeeeee Meeee Me(Me*)Me(eee) ee Meeeeeee:[‌88‌,‌88‌]

MMMMMMM: Meeeeee eee eeeee eeeeee eee eeeeeeeeeee eeeeeeeee.

Me eee eeeeeeeee, eeeeee eee eeeeee eee eeeee eeeee ee eee eeee ee eee eeeeeeee, eeeeeeee ee eee eeeee, ee eee eeeee eee eee eeeeee eeee eeeeeeeee ee eee eeeeeeee eeeeeee eee eee eeeeeeeee eeee eee eeeee ee eee eeee ee eee eeeeeeee. Me(Me*)Me(eee) (8.8 ee, 88 µeee) eee eeeee ee e eeee eeeeeeee eeee e eeeeee eee. Mee eeee eee eeeeee eee eeee eeeeeeeee eee eeeeee eeee M8 eeeee eeeee. Meeeeee (8 eM, eeeeeeee eee 8 e eeee M8 eeeee) eee eeeee, eeeeeeee ee eee eeeeee (8.88 eeee) eee eee eeeee (8.88 eeee). Mee eeeeeee eee eeeeeee ee ee eee 88 eee. Mee eeeeeee eee eeeeeeee eeee eeeeee eee eee eeeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8 ee 8:8).

8-Meeeeeeeeee ee 8,8-Meeeeeeeeeeee 8M-8,8,8-Meeeeeeee ‌8‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee eee eeeee eeeeee eee eeeeeeeeeee eeeeeeeee.

Me eeeeee (8.88 eeee) eee eeeee ee e eeee ee 8-eeeeeeeeee eeeee (888 ee, 8.88 eeee) eee [Me(Me*)Me(MMe8)8] (8.88 e, 8.88 eeee) ee eeeeeee (8.8 eM) (MMMMMMM: eeeeeeeeee). Mee eeeeeee eeeeeee eee eeeeee ee eeeeee eee 8 e, eee eeee eeeeee ee eeeeeee eeeeeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeeee 8:8 ee Me8M eeee) eeeeeeeee eee M-eeeeeeeee 8,8,8-eeeeeeee ‌8‌. Me eeeeee eee 8-eeeeeeeeee eeeeeeeeee eeeee, e 8.8 M eeee ee e-MeMM ee MMM (8.88 eM) eee eeeeee eeeee ee e eeee ee eee M-eeeeeeeee 8,8,8-eeeeeeee ‌8‌ (8.88 eeee) ee MMM (88 eM) ee −88 °M. Mee eeee eee eeeeee eeeeee ee 8 °M eeee e eeeeee ee 8–8 e eee eeee eeeeeeeeeee eeee eeeeeee MeMM (88.8 µM, 8.88 eeee) ee 8 °M. Mee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 88:88).

References