Azides, organotin

S.4.2. by Reaction of an Organotin Azide with a Transition- or inner Transition-Metal-Hydride Complex. 

The use of organotin azides as key reagents in the synthesis of tetrazoles of pharmaceutical interest. ... 

The reaction of diisothiocyanates with sodium azide in water at reflux temperature within 4 hours provides bis(tetrazoHne-5-thiones) as difunctional compounds [136]. If organotin azides hke tri-n-butyltin azide (181) or triph-... 

Scheme 36 The reaction of organotin azides 181 and 182 with phenyl isothiocyanate (183) gives l-phenyl-4-organotin-A -tetrazoline-5-thiones 184 and 185 and their tautomers (S-organotin)-l-phenyl-5-thiotetrazoles 186 and 187. The latter are the confirmed structures of the formed intermediates that upon treatment with dilute hydrochloric acid, provide l-phenyl-A -tetrazoline-5-thione (188) [137,138]...

Molloy et al. have been investigating the use of organotin azides, as such species readily react with nitriles in cycloaddition reactions to give tetrazoles as precursors to functionalized poly-tetrazoles. Those substances can... 

More recently, organotin azides and tin derivatives of hydrazine, 1,3-diphenyltriazene, formamide, urea, isourea, guanidine, amidine, carbo-diimide, carbamic, and thiocarbamic acids, an imidoether and imido-phosphoranes have been prepared, so that now almost every imaginable type of organotin-nitrogen compound has become known. 

Organotin(II) compound 103 reacts with organic azides to yield stable dispiro compounds 104294. This derivatizing reaction may be applicable to different types of organ-otin(II) compounds. Another effective derivatizing possibility is with acetylenic compounds, as shown in reaction 43 (see Table 8)248. 

The reactions with hydrogen cyanide, hydrazoic acid, phosphines, and arsines (Section 16.5) have been used as routes to the organotin cyanides, azides, phosphines and arsines, respectively. Examples are given in the following equations.29... 

Organotin hydrides can be used for the reductive transformation of a variety of functionalities. When an azide was treated with Bu3SnH in the presence of AIBN the azide group was converted to the desired amino group while spiroketal and allyl alcohol components remained intact (Scheme 12.114) [218]. 

Carhon nucleophiles of pXa 10-20 have heen most studied and often work hest with these substrates (eq 1), hut enamines, cyclopentadiene anions, enolates (eq 2), organotin, -thaUium, -zinc, -aluminum, -lithium, and -zirconiums, as weU as Grignards (eq 3) and horates, also add to r-allylpaUadium complexes. Heteroatom nucleophiles also add successfully these include amines (eq 4), amides, azides, magnesium amides, sulfonamides, alcohols, acids (eq 5), nitrites, sulhnic acids, thiols, phosphines, and phosphites. Limited use of transition metal nucleophiles is also known. ... 

This chapter comprises organotin compounds having a pseudohalogen group linked to tin. Aside from (iso)cyanides, (iso)cyanates (iso)thiocyanates and azides reported in the Main Volume, a number of novel derivatives are added. These include (iso)selenocyanate-NCSe, fulminate-CN 0 and N-derivatives of dicyanamide-N(CN)2 and tricyanomethane-N C C(CN)2 The compounds listed in Tables 158 and 159 are prepared by the following methods. 

Tri-n-butyltin hydride/azodiisobutyronitrile Radical reductions with organotin hydrides Carboxylic acid amides from carboxylic acid azides... 

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