Allyltriphenyltin

Allylmagnesium bromide, 41, 49 reaction with acrolein, 41, 49 5-Allyl-l,2,3,4,5-pentachlorocyclopen-tadiene, 43, 92 Allyltriphenyltin, 41, 31 reaction with phenyllithium, 41, 30 Aluminum chloride, as catalyst, for isomerization, 42, 9 for nuclear bromination and chlorination of aromatic aldehydes and ketones, 40, 9 as Friedel-Crafts catalyst, 41, 1 Amidation, of aniline with maleic anhydride, 41, 93... 

Tetranitrofluorenone, 42, 95 Tetraphenyltin from phenyllithium and allyltriphenyltin, 41, 30 Teteolic acid, 42, 97 Thiobenzoylthioglycolic ACID, 42, 100... 

Allyl bromide, in preparation of allyl-magnesium bromide, 41, 49 in preparation of allyltriphenyltin, 41, 31... 

Allyltriphenyltin can also be prepared by using the reaction of preformed allylmagnesium bromide with triphenyltin chloride.2 However, the submitters prefer the simpler procedure described above for large-scale preparations of allyltin compounds. 

Tetraallyltin, triallylphenyltin, and diallyldiphenyltin may be used in place of allyltriphenyltin. 

Alkynyltributyltin reagents, 305 Allyltributyltin, 10, 122, 295, 305 Allyltriphenyltin, 14 Bis(2-pyridinethiolato)tin(II), 40 Bis(tributyltin) oxide, 41 r-Butyl hydroperoxide-Dibutyltin oxide, 53... 

The total synthesis of Stemona alkaloid (-)-tuberostemonine was accomplished by P. Wipf. Late in the synthesis, the introduction of an ethyl sidechain was required. This could be achieved in a novel four-step sequence. First, the allyl sidechain was introduced by the Keck radical allylation. To this end, the secondary alkyl phenylselenide substrate was treated with allyltriphenyltin in the presence of catalytic amounts of AIBN. This was followed by the introduction of a methyl group onto the lactone moiety. The allyl group then was transformed into the desired ethyl group as follows the terminal double bond was isomerized to the internal double bond by the method of R. Roy. This was followed by ethylene cross metathesis and catalytic hydrogenation to provide the desired ethyl sidechain. 

Transmetallation reactions between allyltin compounds and other Lewis acid metal halides (e.g. Bu2SnCl2, BCI3, BBr AICI3, or TiCU) are similarly very fast,39 and the reaction between allyltriphenyltin and BCI3 (though not BF3-OEt2) is complete within one second.40 Reactions of this type have been used for preparing allylic derivatives of boron,41,42 indium,10,38 copper 43 phosphorus, arsenic, antimony,44 and other metals. 

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