Talk:Diazo

The stub should be expanded to consider at least two commercial uses. At the N2 bond diazo compounds readilly combine, or couple, to form new compounds. Many of these are colored. By choice the diazo was water soluble, the dye is water insoluble. This was a 19th century method of fast dying fabrics. Many diazo compounds are light sensitive at 350 to 450 nm. The bond is broken and the tar produced does not couple. This was a the basis of a copying process that replaced blueprints. This process is currently in diminishing use.

I worked in the reprographic industry, as a physicist, from 1954 to 1982. I will help page preparation on this, but it has to be led by a chemist.

regnim


 * Hi Regnim, why don't you just start the edit you intend to make, there are plenty of chemists around keeping an eye on this page who will glad to be of assistance V8rik 22:20, 22 December 2005 (UTC)

PS 4 tildes (~) in a row will print a name and a date together with your remark.

azo / diazo

 * Can someone clear up the relationship between the terms 'diazo' and azo compound? And does the 'di' in 'diazo' mean anything.  Is there a different 'azo' functional group? ike9898 14:53, 28 July 2006 (UTC)

ChristianB (talk) 02:46, 22 November 2007 (UTC)
 * diazo is the functional group R=N(+)=N(-) e.g. CH2=N2. azo (which is the same as diimide) is the functional group (-)N=N(-). In inorganic chemistry you have: amide (R2N(-)) and imide (RN(2-)) and boths are something completly different in organic chemistry.

diazocoupling
Can someone define diazocoupling? --Abdull (talk) 10:43, 18 November 2007 (UTC)

Resonance sturucture is missing the 1,3-dipole
It should be:  N(+)=N-C(-)R2 I think that resonance structure is important because its explains why its react as a 1,3-dipolar ChristianB (talk) 02:46, 22 November 2007 (UTC)
 * Taken care of V8rik (talk) 20:26, 27 March 2009 (UTC)

Hazard of the diazo compound
Should there be information about the potential hazards of diazo compounds? My organic chemistry professor was just talking about it being really prone to explosion and hazardous to human health if inhaled, but I'm not too sure I have grasped the whole idea enough to explain it. E-Ping Rau 04:06, 31 December 2009 (UTC)

Diazo transfer
The figure shows a diazo transfer but the reagent is definitely not tosyl azide...and I am skeptical that a diazo transfer would even occur using phenyl azide. Perhaps a new figure should be made. — Preceding unsigned comment added by 98.23.237.165 (talk) 03:33, 15 October 2011 (UTC)

Mechanism of N-alkyl-N-nitroso(sulfon)amide fragmentation to form diazoalkanes
I feel that the mechanism shown is probably not the right one (although I cannot be certain). Older sources will indeed suggest the mechanism shown for the formation of diazomethane from nitrosocarbamates and ureas. This is based on the thermal decomposition of these compounds in the absence of base to ultimately form an ester and dinitrogen. However, in the presence of base, attack on the sulfonamide S is probably more facile. Except for Diazald (which only reacts at >55 deg C), most carbamate and urea based nitrosoamides actually produce diazomethane at 0 to -5 deg C (ref: https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.19800630416). These conditions result in fast reactions and are considerably milder than the conditions at which the 1,2-rearrangement and decomposition to form ester and dinitrogen occur (ref: https://pubs.acs.org/doi/abs/10.1021/ja01627a065). Although I don't think the mechanistic data is definitive -- in fact March and Smith 6th ed shows this mechanism -- I tend to favor the mechanism shown on the Diazald page. I guess the question is, which mechanism should be shown in the absence of definitive mechanistic data? Alsosaid1987 (talk) 03:21, 26 July 2018 (UTC)