104174-74-5Relevant articles and documents
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Kingsbury,C.A.
, p. 1319 - 1323 (1970)
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A sequential o-nitrosoaldol and grignard addition process: an enantio- and diastereoselective entry to chiral 1,2-diols
Jiao, Peng,Kawasaki, Masanori,Yamamoto, Hisashi
supporting information; experimental part, p. 3333 - 3336 (2009/09/26)
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Cyclocondensation of oxalyl chloride with 1,2-glycols
Iida,Itaya
, p. 10511 - 10530 (2007/10/02)
Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-l, and erythro-1,2-disubstituted ethylene glycols 1f, m, o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n, p, q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate of the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.
