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Volumn 69, Issue 1, 2004, Pages 33-45

An Approach toward Azacycles Using Photochemical and Radical Cyclizations of N-Alkenyl Substituted 5-Thioxopyrrolidin-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ELECTRON ENERGY LEVELS; FREE RADICALS; IRRADIATION; PHOTOCHEMICAL REACTIONS; REDUCTION; X RAY ANALYSIS;

EID: 0347361527     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035127w     Document Type: Article
Times cited : (16)

References (133)
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    • note
    • We have deposited atomic coordinates for compounds 17 and 47b with the Cambridge Data Centre. The coordinates can be obtained on the request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, U.K.
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    • note
    • It is also conceivable that 36 is formed by a mechanism similar to that outlined in path B, Scheme 11 for the conversion of thiomaleimide 46 to 47.
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    • note
    • Another possibility to account for the preference of the trans diastereomer was suggested by one of the referees. The trans product could form from an exo approach of the cycloalkene ring to the electronically excited heterocyclic ring and the cis product from an endo approach of the two reacting sites. The difference in energy of the respective transition states would also explain the preference for the trans diastereomer.
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    • (b) We have used the UNIX version of PCModel operating on a G4-Macintosh computer (OSX 10.2) for these calculations.
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    • note
    • We assume that the conversion of 25 to 26 also occurs via a similar diradical intermediate.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.