ChemInform Abstract: ELECTROPHILIC HETEROCYCLIZATION OF UNCONJUGATED DIENES. (REVIEW)

GEVAZA, YU. I.; STANINETS, V. I.

doi:10.1002/chin.198452379

Chemischer Informationsdienst

1984

DOI: 10.1002/chin.198452379

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ChemInform Abstract: ELECTROPHILIC HETEROCYCLIZATION OF UNCONJUGATED DIENES. (REVIEW)

YU. I. GEVAZA¹,

V. I. STANINETS²

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2011

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“…Below are given the results of our study on the reaction of an isolated diene, cycloocta-1,5-diene (1,5-COD), with trifluoromethanesulfonamide in the oxidative system t-BuOClNaI · 2 H 2 O. Cycloocta-1,5-diene is known not only as ligand for complexation with transition metals but also as important synthon for design of various carbo-and heterocycles. Electrophilic transannular addition to 1,5-COD could give rise to bicyclic compounds of three types, bicyclo[3.3.0]octanes [5], 9-heterobicyclo[3.3.1]-nonanes [6][7][8][9][10][11], or mixtures of the latter with isomeric 2,5-disubstituted 9-heterobicyclo[4.2.1]nonanes [12][13][14][15][16][17][18][19][20][21][22][23][24][25] (Scheme 3). We have found no published data on the synthesis of fluorinated azabicyclononanes from 1,5-COD.…”

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Reaction of trifluoromethanesulfonamide with alkenes and cycloocta-1,5-diene under oxidative conditions. Direct assembly of 9-heterobicyclo[4.2.1]nonanes

2011

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Reactions of trifluoromethanesulfonamide with α-methylstyrene, 2-methylpent-1-ene, and cycloocta-1,5-diene in the system t-BuOCl-NaI were studied. In the reaction with α-methylstyrene 1-iodo-2-phenylpropan-2-ol was the only isolated product. The reaction with 2-methylpent-1-ene gave a mixture of N,N′-(2-methylpentane-1,2-diyl)bis(trifluoromethanesulfonamide), trifluoro-N-(2-hydroxy-2-methylpentyl)-methanesulfonamide, and N, N′-[oxybis(2-methylpentan-2,1-diyl)]bis(trifluoromethanesulfonamide). Trifluoromethanesulfonamide reacted with cycloocta-1,5-diene to produce a mixture of 2,5-diiodo-9-(trifluoromethylsulfonyl)-9-azabicyclo[4.2.1]nonane and 2,5-diiodo-9-oxabicyclo[4.2.1]nonane; this reaction may be regarded as the first example of direct assembly of bicyclononane skeleton.We recently showed that aziridination of styrene with trifluoromethanesulfonamide in the oxidative system t-BuOCl-NaI · 2 H 2 O leads to formation of both linear structures I and II and heterocyclization product, 2,5-diphenyl-1,4-bis(trifluoromethylsulfonyl)piperazine (III) [1]. The structure of III was proved by X-ray analysis, and a mechanism involving intermediate formation of 2-phenyl-1-trifluoromethylaziridine was proposed [1]. However, the formation of substituted piperazine instead of expected aziridine contradicted the data reported by Minakata et al. [2], according to which aziridines were obtained in reactions of styrene and other alkenes with sulfonamides under analogous conditions due to strong electron-withdrawing effect of the CF 3 group [1]. We tried to reproduce the conditions described in [2] more accurately and carried out the reaction of styrene with trifluoromethanesulfonamide in the presence of anhydrous sodium iodide. In this case, we isolated compounds I and II and 2,6-diphenyl-1,4-bis(trifluoromethylsulfonyl)piperazine (IV) which is isomeric to III [3].In the present work we studied reactions of trifluoromethanesulfonamide with α-methylstyrene, 2-methylpent-1-ene, and cycloocta-1,5-diene under oxidative conditions (in the presence of t-BuOCl-NaI or t-BuOCl-NaI · 2 H 2 O) and analyzed possible ways of formation of the corresponding products.Taking into account that α-methylstyrene reacted with trifluoromethanesulfonamide in a way similar to styrene [2], i.e., with formation of the corresponding aziridine, and that the reaction direction strongly depends on the composition of the oxidative system, α-methylstyrene (V) was brought into reaction with trifluoromethanesulfonamide in two systems containing NaI · 2H 2 O or anhydrous NaI (as in [2]). In both cases, the only product was 1-iodo-2-phenylpropan-2-ol (VI) (Scheme 1). Compound VI is likely to be formed via iodination of α-methylstyrene with t-BuOI to

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Reaction of trifluoromethanesulfonamide with alkenes and cycloocta-1,5-diene under oxidative conditions. Direct assembly of 9-heterobicyclo[4.2.1]nonanes

2011

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ChemInform Abstract: ELECTROPHILIC HETEROCYCLIZATION OF UNCONJUGATED DIENES. (REVIEW)

Cited by 1 publication

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Reaction of trifluoromethanesulfonamide with alkenes and cycloocta-1,5-diene under oxidative conditions. Direct assembly of 9-heterobicyclo[4.2.1]nonanes

Reaction of trifluoromethanesulfonamide with alkenes and cycloocta-1,5-diene under oxidative conditions. Direct assembly of 9-heterobicyclo[4.2.1]nonanes

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