THE FRAGMENTATION OF 2,3-DIHYDROISOTHIAZOL-3-ONE 1,1-DIOXIDE DERIVATIVES - A NOVEL CHELETROPIC PROCESS

Adducts obtained by 1,3-dipolar cycloadditions to 2,3-dihydroisothiazol-3-one 1,1-dioxides are inclined to undergo a cheletropic process, by which the newly formed heterocyclic part undergoes aromatization, while SO2 is extruded and an isocyanate is generated. The isocyanates are stable under the co...

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Bibliographic Details
Published inChimia Vol. 46; no. 7-8; pp. 335 - 337
Main Author BURRI, KF
Format Journal Article
LanguageEnglish
Published BASEL NEW SWISS CHEMICAL SOC 01.07.1992
Swiss Chemical Society
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
TILCOTIL
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Summary:Adducts obtained by 1,3-dipolar cycloadditions to 2,3-dihydroisothiazol-3-one 1,1-dioxides are inclined to undergo a cheletropic process, by which the newly formed heterocyclic part undergoes aromatization, while SO2 is extruded and an isocyanate is generated. The isocyanates are stable under the conditions of their formation, and are subject to standard isocyanate reactions. The process might be employed to synthesize isocyanates and derivatives of urethanes, ureas etc., whenever the use of mild and neutral reaction conditions is dictated by the sensitivity of the intermediates and products involved.
ISSN:0009-4293
2673-2424
DOI:10.2533/chimia.1992.335