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Updated: Aug 8, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
The adduct of di-μ2-hydroxido-bis-[chlorido-di-phenyl-tin(IV)] with two mol-ecules of 2-vinyl-pyridine
Tobias Gieschen1, Hans Reuter1
1Chemistry, Osnabrück University, Barabarstr. 7, 49069 Osnabrück, Germany.
Abstract:
The solid-state structure of the adduct of di-phenyl-tin(IV) hydroxide chloride, Ph2Sn(OH)Cl, with 2-vinyl-pyridine, 2Vipy, namely, di-μ-hydroxido-bis-[chlorido-diphenyl-tin(IV)]-2-ethenyl-pyridine (1/2), [Sn2(C6H5)4Cl2(OH)2]·2C7H7N, exhibits dimeric, hydrogen-bonded aggregates [Ph2Sn(OH)Cl·2Vipy]2. The aggregates are non-centrosymmetric but exhibit the characteristic structural features of Brønsted base, BB, stabilized diorganotin(IV) hydroxide-halides, [R 2Sn(OH)Hal·BB]2, with trigonal-bipyramidally coordinated tin atoms and two bridging hydroxide groups. Non-centrosymmetry leads to a slightly bent and distorted rhombic, four-membered Sn2-O2 ring consisting of two different tin and oxygen atoms. As usual, Sn-O bond lengths depend on the position the hydroxyl groups adopt within the trigonal-bipyramidal coordination sphere of the Sn atoms [mean values: d(Sn-OH)ax = 2.191 (9) Å, d(Sn-OH)eq = 2.019 (3) Å]. Bond angles within the Sn2-O2 ring are acute [mean value: 71.1 (2)°] at the tin atoms and obtuse [mean value: 108.9 (3)°] at the oxygen atoms. Hydroxyl groups display a trigonal-planar constitution and are involved in hydrogen bonds [mean values: d(O⋯N) = 2.714 (8) Å; <(O-H⋯N) = 170 (5)°] to the N atoms of the 2-vinyl-pyridine mol-ecules.
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