Reaktivität und Toxizität cyclischer Schwefelsäur eester

Fischer, Gerhard W.; Jentzsch, Renate; Kasanzewa, Valentina; Riemer, Fritz

doi:10.1002/prac.19753170610

Cited by 18 publications

(1 citation statement)

References 14 publications

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“…4 Cyclic sulfates undergo regioselective nucleophilic substitutions when reacted with O-nucleophiles, [4][5][6][7][8] S-nucleophiles, [6][7][8][9] halide nucleophiles, 8,10,11 C-nucleophiles, 6,12 and N-nucleophiles. 4,7,8,13 Cyclic sulfates are readily prepared through the oxidation of cyclic sulfites, which are obtained in very good yield by reaction of diols with thionyl chloride. 6 Carbohydrate cyclic sulfates are usually synthesized from a suitable protected carbohydrate precursor.…”

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Regiospecific Synthesis of New Methyl Sulfoglucopyranoside-Based Surfactants: Nucleophilic Displacement of a Cyclic Sulfate

Bazin¹,

Linhardt²

1999

Synthesis

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A two-step regiospecific synthesis of a new class of anionic and amphoteric methyl a-D-glucopyranoside-based surfactants is described. Reaction of methyl a-D-glucopyranoside with thionyl chloride followed by oxidation of the resulting sulfite afforded the corresponding methyl a-D-glucopyranoside 4,6-cyclic sulfate in high yield. Nucleophilic displacement of this cyclic sulfate by different fatty acids and amines led to the corresponding methyl 6-O-acyl-or 6-amino-6-deoxy-4-sulfoglucopyranosides in very good yields. These newly synthesized sulfoglucopyranosidebased surfactants displayed low critical micelle concentration (CMC) values.

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mentioning

confidence: 99%

Regiospecific Synthesis of New Methyl Sulfoglucopyranoside-Based Surfactants: Nucleophilic Displacement of a Cyclic Sulfate

Bazin¹,

Linhardt²

1999

Synthesis

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Sulfuric and Sulfurous Esters

McCormack

Lawes

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Sulfuric and sulfurous acids form a series of esters analogous to those from other acidic materials. The hydrogen of the acid is replaced by a carbon‐containing group. Because two hydrogens are present in the sulfur‐based acids, there are two series of esters. Replacement of one hydrogen results in an acid ester. If both hydrogens are replaced, whether with the same, with different, or with bifunctional substituents, symmetrical and unsymmetrical diesters form. Dimethyl sulfate, diethyl sulfate, and long‐chain monoalkyl alkali metal sulfates are the compounds of practical interest. Dialkyl sulfates have been used to introduce a methyl or ethyl group into a wide variety of organic compounds. The long‐chain monoalkyl hydrogen sulfates, in the form of their alkali metal or alkylammonium salts, are valuable as surface‐active agents and are used commercially. The short‐chain monoalkyl hydrogen sulfates are intermediates in commercial conversion routes from olefins to alcohols.

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