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Volumn , Issue 10, 1999, Pages 1582-1584

An unprecedented coupling reaction of arylmagnesium compounds with tetrahydrofuran providing 2-aryltetrahydrofuran mediated by an iodoalkane- EtMgBr system

Author keywords

Coupling; Iodine; Magnesium; Radical reactions; Tetrahydrofuran

Indexed keywords

MAGNESIUM DERIVATIVE; TETRAHYDROFURAN;

EID: 0032846896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2915     Document Type: Article
Times cited : (35)

References (35)
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    • Silverman, G. S.; Rakita, P. E. Eds.; Marcel Dekker: New York
    • b) Handbook of Grignard-Reagents; Silverman, G. S.; Rakita, P. E. Eds.; Marcel Dekker: New York, 1996.
    • (1996) Handbook of Grignard-Reagents
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    • a) Boymond, L.; Rottl̈ander, M.; Cahiez, G.; Knochel, P. Angew. Chem. 1998, 110, 1801; Angew. Chem. Int. Ed. Engl. 1998, 37, 1701.
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  • 11
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    • Recently, synthetic applications of transition metal-catalyzed radical reaction involving Grignard reagents have been reported. a) Terao, J.; Saito, K.; Nii, S.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1998, 120, 11822.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11822
    • Terao, J.1    Saito, K.2    Nii, S.3    Kambe, N.4    Sonoda, N.5
  • 18
    • 0022531932 scopus 로고
    • c) Brückner, C.; Lorey, H.; Reisig, H.-U. Angew. Chem. Int. Ed. Engl. 1986, 25, 556; Angew. Chem. 1986, 98, 559.
    • (1986) Angew. Chem. , vol.98 , pp. 559
  • 20
    • 0345539198 scopus 로고    scopus 로고
    • note
    • The use of i-PcI instead of EtI provided 1a in decreased yield (28%).
  • 25
    • 0345107742 scopus 로고    scopus 로고
    • note
    • The use of other solvents in place of THF gave quite unsatisfactory results. Using 2-methyltetrahydrofuran as a solvent, 2-methyl-2-thienyltetrahydrofuran and 2-methyl-5-thienyltetrahydrofuran were obtained in 12% and 23% yields, respectively. The reaction in tetrahydropyran provided 2-thienyltetrahydropyran in only 18% yield under the same reaction conditions.
  • 35
    • 0345107739 scopus 로고    scopus 로고
    • note
    • 2: C, 74.13; H, 7.92.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.