LIII.—Experiments on the production of compounds containing arsenic as a centre of optical activity

Through a Glass Darkly—Some Thoughts on Symmetry and Chemistry

“…Chiral stibanes have attracted relatively little interest, although the first optically pure compounds were described in the 1940s and 1950s [204][205][206][207][208][209]. Early studies at resolving [AsR 1 R 2 R 3 R 4 ] + arsanium salts were partially successful [210] although they racemized very rapidly. In 1925, the first arsane sulfide, EtMe(HO 2 CC 6 H 4 )AsS, was resolved [211].…”

2 Advances in organic chemistry over the last 100 years

“…33 Some trisubstituted phosphine oxides had been resolved by Meisenheimer et al early in the century. 34 However most progress had to wait until the 1950s when phosphonic acids and their derivatives became more available and interest in phosphorus chemistry had been intensified by industrial uses of phosphorus compounds, as extractants by the atomic energy industry, in systemic insecticides, plasticisers and as phosphate detergents. Within a few years numerous compounds appeared owing their activity to an asymmetric phosphorus atom.…”

“…Optically active four-bonded arsenic compounds had been known since the 1920s, as methylphenylbenzyl-1-naphthylarsenonium iodide. 34 Campbell prepared the first optically active stibine (6) in 1955, 35 but she had slightly earlier resolved a number of compounds with antimony or arsenic atoms unable to invert by being part of a heterocyclic ring. In the 1940s much work was done by Mann on optical activity due to a hetero-atom, including the resolution of analogues of tetralin containing arsenic (7), antimony, selenium and sulfur as ring atoms.…”

Smoke-forming Chemicals.

“…The ratio r = 0.54, and about 5 per cent of sulfuric acid is formed. Upon distillation under reduced pressure of the mixture of sulfate and chlorosulfonic acid about 50 per cent of the methyl chlorosulfonate is recovered, the chlorosulfonic acid is practically all lost, and sulfuric acid accumulates up to 20 per cent (41).…”