Abstract
Sulfur-functionalized methyltin compounds
nBu
3SnCH
2S(O)
i
R (
i=0, 1, 2; R=Me, Ph) underwent transmetallation with Grignard compounds MgR′X (R′=Me,
nBu, Ph; X=Cl, Br, I) and diorganomagnesium compounds MgR′R″ (R′/R″=Me/Me,
nBu–
sBu) to provide Sn(
nBu)
3R and Mg[CH
2S(O)
i
R]X and Mg[CH
2S(O)
i
R]R″, respectively. Analogously, the reaction of
nBu
3SnCH
2P(O)Ph
2 with Mg(
nBu)Br afforded quantitatively Mg[CH
2P(O)Ph
2]Br and Sn(
nBu)
4. Transmetallations between
nBu
3SnCH
2YMe
2 (Y=N, P) and MgMe
2 proceeded only in the presence of catalytic amounts (10–20 mol%) of Li
nBu yielding Mg(CH
2YMe
2)Me and Sn(
nBu)
3Me/Sn(
nBu)
4.
Functionalized methyltin compounds underwent transmetallation with Grignard and diorganomagnesium compounds, MgR′X and MgR′R″, respectively, to provide corresponding functionalized methylmagnesium compounds, see Scheme. Furthermore, it was shown that analogous reactions between
nBu
3SnCH
2YMe
2 (Y=N, P) and MgMe
2 can be enforced to proceed by catalytic amounts of butyllithium.