Curtius rearrangement reaction

In 1885, German chemist Theodor Curtius reported the thermal decomposition of an acyl azide to an isocyanate, with the loss of nitrogen. This reaction subsequently became known as the Curtius rearrangement. Compared with the uncatalyzed reaction, acid catalysis through the use of either protic or Lewis acids significantly lowers the required reaction temperature, allowing for the use of more delicate substrates.

The acyl azide precursors can be made through several methods, including reacting acid chlorides or mixed anhydrides with alkali azide or trimethylsilyl azide, treating acylhydrazones with nitrous acid or nitrosonium tetrafluoroborate, or treating carboxylic acids with diphenyl phosphoryl azide (DPPA). If the reaction is carried out in the presence of water, amines, or alcohols, then the corresponding amines, ureas, and carbamates are formed.

It is possible to induce the Curtius rearrangement through the use of photochemical conditions—this is known as the Harger reaction.

The Curtius rearrangement has been successfully employed in several total synthesis campaigns including that of the antitumor and antibacterial streptonigrone, as well as pancratistatin, another compound with potent antitumor and antiviral activities.

Review available Thermo Scientific products for the Curtius rearrangement reaction:

Catalog # Name Size Price (USD) Qty
J21610.22 Sodium Azide, ≥99% Each
76.50
L00173.14 Trimethylsilyl azide, 94% Each
101.65

Special offer

Online exclusive

119.00
Save 17.35 (15%)
L00173.06 Trimethylsilyl azide, 94% Each
35.65

Special offer

Online exclusive

42.20
Save 6.55 (16%)
A12124.06 Diphenylphosphonic azide, 97% Each
25.65

Online Exclusive

28.60
Save 2.95 (10%)
J21610.36 Sodium Azide, ≥99% Each
152.65

Special offer

Online exclusive

179.00
Save 26.35 (15%)
A12124.14 Diphenylphosphonic azide, 97% Each
79.65

Special offer

Online exclusive

94.10
Save 14.45 (15%)
A15806.04 Nitrosonium tetrafluoroborate, 98% Each
42.65

Online Exclusive

47.50
Save 4.85 (10%)
A15806.18 Nitrosonium tetrafluoroborate, 98% Each
344.65

Special offer

Online exclusive

405.00
Save 60.35 (15%)
A15806.09 Nitrosonium tetrafluoroborate, 98% Each
96.65

Special offer

Online exclusive

113.00
Save 16.35 (14%)
J21610.A1 Sodium azide, 99+% Each
310.65

Special offer

Online exclusive

365.00
Save 54.35 (15%)
A13651.AP Chlorotrimethylsilane, 98% Each
56.65

Special offer

Online exclusive

66.10
Save 9.45 (14%)
A18668.0I Sodium nitrite, 98% Each
187.65

Special offer

Online exclusive

220.00
Save 32.35 (15%)
A12124.22 Diphenylphosphonic azide, 97% Each
187.65

Special offer

Online exclusive

220.00
Save 32.35 (15%)
A13651.AE Chlorotrimethylsilane, 98% Each
29.65

Special offer

Online exclusive

34.20
Save 4.55 (13%)
L00173.22 Trimethylsilyl azide, 94% Each
309.65

Online Exclusive

344.00
Save 34.35 (10%)
A13651.AC Chlorotrimethylsilane, 98% Each
23.65

Online Exclusive

26.10
Save 2.45 (9%)
A18668.0B Sodium nitrite, 98% Each
66.65

Special offer

Online exclusive

78.00
Save 11.35 (15%)

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