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Reaction of bicyclo[3.2.1]octadiene with 4-methyl-1,2,4-triazoline-3,5-dione: competitive dipolar and homo-cycloaddition

โœ Scribed by Waldemar Adam; Ottorino De Lucchi

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
226 KB
Volume
22
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The nonconjugated bicyclo[3.2.l]octa-2,6-diene (1) affords with 4-methyl-1,2,4-triazolin-3,5-dione (MTAD) the homo-cycloadduct (2) product and the rearranged urazoles ( 2) and ( 2) through dipolar cycloaddition, while ene-reaction and (2+2)-cycloaddition are not observed.

Bicyclo[3.2.l]octa-2,6-diene ($), although a nonconjugated diene and thus incapable of (2+4)-cycloaddition, is nevertheless expected to show a great diversity of dienophilic reactivity. For example, it could react with 4-me-

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In a continuing study of cycloaddition reactions involving cyclopropane ring-containing systems (1) we have investigated the reactions of vinylcyclopropane and some substituted vinylcyclopropanes with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and chlorosulfonylisocyanate (CSI).