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Extra resources for Chemins vers l'analyse (Exercices Vuibert)
Bragg, Jones, and Turner proved that the mannitol derivative possesses a five-membered ring by cleaving the hydrolysis product with periodic acid, but they presented no evidence to substantiate their suggestion that the compound is 4,5-bis(l, 2-dichloroethyl)-1, 3, 2-dioxathiolane 2,2-dioxide (2la). [For references, see pp. ] 17 Chapter 1 2, 5-O-Methylene-~-mannitol forms a trichloro derivative rather than a chlorinated sulfate. Sugar derivatives are discussed in section VII. Ham48br48c found that treatment of ethylene oxide with the dioxanesulfur trioxide complex yields a heavy oil.
Bunton, de la Mare, and c o - ~ o r k e r s ~ ~ ? 2 2studied * 2 3 both the alkaline and acid hydrolysis of ethylene sulfite. The alkaline hydrolysis was too [For references, see pp. ] 11 Chapter 1 fast to be measured by their technique, but the much slower acid hydrolysis was investigated in detail. The mechanism was pictured as follows: HOCHzCHzOH + SO2 The evidence for their mechanism is discussed in Chapter 8, section I A-la-(3). Suffice it to say here that DavisSla found the heats of hydrolysis of ethylene suIfite and dimethyl sulfiteJo be identical, a s did Pagdin, Pine, and co-workers,64a for ethylene sulfite and trimethylene sulfite.
Baker and Fieldla prepared ethylene sulfate (20)by reacting ethylene dibromide with silver sulfate. AgzSO, BrCH2CH,Br xylene, ref'ux 23% ~ cy 20 According to Brimacombe, Foster, and c o - w ~ r k e r s , ~the ~ Creaction fails with 1,2-dibromopropane. Garner and Lucas41 prepared trans4, 5-dimethyl-1, 3,2-dioxathiolane 2,2-dioxide (21) by oxidizing the cyclic sulfite ester of ~-(-)-2, 3-butanediol with calcium permanganate. Ca(YnO4l2, AcOH 15" CH3f0-,,, 45% CH3 21 Lichtenberger and H i n ~ k yprepared ~ ~ ~ the cis isomer from meso-2, 3butanediol in 54% yield.
Chemins vers l'analyse (Exercices Vuibert) by Francis Pecastaings, Jacky Sevin