The acetates of the methyl hemiacetals of alpha-halo aldehydes, 1, easily undergo nucleophilic attack by lithium thiolates or ethane dithiolate affording alpha-thioalkyl aldehydes 2 or 2-hydroxy-1,4-dithianes 3, respectively. 3-monosubstituted dithianes 3 smoothly dehydrate to 2,3-dihydro-1,4-dithiines 4, whereas 3,3-disubstituted derivatives give dimers 6. The single-crystal X-ray analysis of 6b shows that it crystallises in a racemic form, with the dithiane ring in a chair conformation and the exocyclic S(3) atom axially bonded to the ring. The crystal packing appears to be determined mainly by a weak C-H ... O hydrogen bonding interaction.

The reaction of the acetates of alpha-chloro methyl hemiacetals with nucleophiles. Synthesis of 2-hydroxy-1,4-dithianes / L., Antolini; Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 127:(1997), pp. 11-17.

The reaction of the acetates of alpha-chloro methyl hemiacetals with nucleophiles. Synthesis of 2-hydroxy-1,4-dithianes

BELLESIA, Franco;GHELFI, Franco;PAGNONI, Ugo Maria;PINETTI, Adriano
1997

Abstract

The acetates of the methyl hemiacetals of alpha-halo aldehydes, 1, easily undergo nucleophilic attack by lithium thiolates or ethane dithiolate affording alpha-thioalkyl aldehydes 2 or 2-hydroxy-1,4-dithianes 3, respectively. 3-monosubstituted dithianes 3 smoothly dehydrate to 2,3-dihydro-1,4-dithiines 4, whereas 3,3-disubstituted derivatives give dimers 6. The single-crystal X-ray analysis of 6b shows that it crystallises in a racemic form, with the dithiane ring in a chair conformation and the exocyclic S(3) atom axially bonded to the ring. The crystal packing appears to be determined mainly by a weak C-H ... O hydrogen bonding interaction.
1997
127
11
17
The reaction of the acetates of alpha-chloro methyl hemiacetals with nucleophiles. Synthesis of 2-hydroxy-1,4-dithianes / L., Antolini; Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 127:(1997), pp. 11-17.
L., Antolini; Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/306109
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