Organotin deuterides

The NMR spectrum of the threo + erythro mixture of methylphenyl(2-phenyl-propyl)tin hydride (51), another compound with two asymmetric atoms, shows two CH3Sn signals (Av = 6.6 Hz in benzene at 270 MHz) which remain aniso-chronous even in the presence of HMPA 22>. The analogous erythro + threo tri-organotin deuteride (52) shows two CH3Sn signals too (Av = 1.5 Hz at 60 MHz... 

The most commonly used method for synthesizing organotin hydrides with a hydrogen isotope bonded to the tin atom is to reduce the appropriate chlorostannanes with labelled hydride reagents, such as lithium aluminium deuteride or sodium borodeuteride. For example, tributylchlorostannane can be reduced with lithium aluminium deuteride42-45 or deuterated or tritiated sodium borohydride46 to give tributyltin deuteride and tritiated tributyltin hydride, respectively (equations 40 and 41). 

Many other groups can be selectively reduced by organotin hydrides. Although these reactions have not been used to date to form labelled compounds, the reactions are included here using tributyltin deuteride as the reducing agent to illustrate the synthetic possibilities for this reagent. 

Although organotin deuterides result from reaction of the chloride and LiAFH or from RsSnNa and HgO, better yields are given by halide/deuteride exchange [equation (8)]. Bu ,Sn H is best prepared from the tin-Grignard reagent (17) using HaO [equation (9)]. ... 

Organotin deuterides may contain deuterium linked to tin or also in the organic moiety. The only novel synthetic method for an organotin deuteride listed in Table 125 is soIvolysis of BusSnNas with D2O leading to BusSnDs ... 

Tetrabromoadamantane - 1,3 5 7-D4-adamantane (l553a). Other organotin deuterides are listed in Table 123. 

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