Organotin-nitrogen compounds preparation

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. 

Tin-nitrogen bonded compounds are generally formed by reaction of an alkali or alkaline earth metal amide with an organotin halide compounds of the types R Sn(NR2)4 , (n = 1-3), (R3Sn) NR 3 (n = 1-3), and cyc/o-(R2SnNR ) (n = 2 or 3) can be prepared (equation 79). Other routes include transaminations (equations 80 and 81). Tin carboxamides and sulfonamides have been obtained by reaction of tin oxides or hydroxides with amides (equation 82). 

Preparation of nitrogen polycyclic compounds using organotin reagents 91YGK128. 

The aminostannanes are usually prepared by transmetallation between an organotin compound such as a halide and an aminometallic compound by transamination of a stannylamine by addition of a tin reagent to a multiple bond to nitrogen, or by an ene reaction (equations 16-1-16-4). The Sn-N bond which is formed is very reactive towards moisture and carbon dioxide, and the reactions must be carried out in an inert atmosphere. 

Amidostannanes containing the groups Sn-NC(=0)R or Sn-NS(0)2R are easier to prepare and to handle than are the aminostannanes. The acidity of the proton on nitrogen in the parent amide is now sufficient for reaction to occur with organotin hydroxides, oxides, and alkoxides (and aminotin compounds), and, once formed, the amidostannanes are less sensitive to moisture. A variety of amidostannanes is also available from the addition of Sn-0 and Sn-N bonded compounds to nitrogen heterocumulenes. 

In 1962 the field of organotin amine chemistry was at last opened up with the publication of four papers (53, 54, 55, 56) on the preparation of compounds of general formula i Sn(NR R")4 covering all possibilities from = 0 to n = 3. In one of these papers (56), moreover, compounds with more than one tin atom joined to the same nitrogen atom, as well as a cyclic compound of the formula [R2SnNR ]3, were described. 

Only a relatively few organotin-substituted heterocycles are known as compared with the large number of organotin-substituted aliphatic and aromatic compounds. Those described in this section, i.e. compounds with an organotin group joined to a nitrogen atom which is contained in a ring, were unknown until 1962. In that year Luijten, Janssen, and Van der Kerk (J, 42) reported the preparation and properties of a number of these compounds. 

This chapter includes organotin derivatives having two tin atoms linked by a hydrocarbon chain. Heteroatoms like halogen, oxygen, nitrogen and phosphorus may be substituted at or in the chain. The compounds listed in Table 117 are prepared by methods from the following scheme. 

The organotin metal imides are all listed in Table 2. The compounds contain lithiiim, germanixun and silicon bound to nitrogen. A scheme for preparation of the organotin metal imides follows. 

---