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Volumn , Issue 4, 1998, Pages 671-678

Synthesis of o-Dialkenylbenzenes and Indenes Using Heck and Oxypalladation Reactions

Author keywords

Arenes, dialkenyl N; Cross coupling, Heck; Indanes; Palladium catalysis

Indexed keywords


EID: 2142711913     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199804)1998:4<671::AID-EJOC671>3.0.CO;2-R     Document Type: Article
Times cited : (25)

References (52)
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    • Diethylbenzene is an industrial product, however, the commercial mixture contains only traces of 1,2-diethenylbenzene (3a). Heck reported for the same reaction 78% of diethenylbenzene apart from 12% of 2-bromostyrene (2a-Br): J. E. Plevyak, R. F. Heck, J. Org. Chem. 1978, 43, 2454-2456.
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    • note
    • With a chiral, nonracemic catalyst an enantioselective synthesis of 12 is conceivable. Further work along these lines is in progress.
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    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100030. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code + (1223) 336-033; e-mail: deposit@ccdc.cam.ac.uk).
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    • o-Iodostyrene 2a-I has been prepared from o-iodobenzaldehyde, but experimental details were not disclosed: R. Morrin Acheson, G. C. M. Lee, J. Chem. Soc., Perkin Trans. 1 1987, 2321-2332. Compound 2a-I has also been prepared by dehydration of 1-(2-iodophenyl)ethanol: M. M. Koton, E. M. Moskwina, Zh Prikl. Khim. (Leningrad) 1953, 26, 660; J. Appl Chem. USSR (Engl. Transl.) 1953, 26, 617.
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    • o-Iodostyrene 2a-I has been prepared from o-iodobenzaldehyde, but experimental details were not disclosed: R. Morrin Acheson, G. C. M. Lee, J. Chem. Soc., Perkin Trans. 1 1987, 2321-2332. Compound 2a-I has also been prepared by dehydration of 1-(2-iodophenyl)ethanol: M. M. Koton, E. M. Moskwina, Zh Prikl. Khim. (Leningrad) 1953, 26, 660; J. Appl Chem. USSR (Engl. Transl.) 1953, 26, 617.
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    • o-Iodostyrene 2a-I has been prepared from o-iodobenzaldehyde, but experimental details were not disclosed: R. Morrin Acheson, G. C. M. Lee, J. Chem. Soc., Perkin Trans. 1 1987, 2321-2332. Compound 2a-I has also been prepared by dehydration of 1-(2-iodophenyl)ethanol: M. M. Koton, E. M. Moskwina, Zh Prikl. Khim. (Leningrad) 1953, 26, 660; J. Appl Chem. USSR (Engl. Transl.) 1953, 26, 617.
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    • 1,2-Dipropenylbenzene was previously obtained as a mixture of cis,cis, cis,trans and trans,trans isomers by Wittig olefination of phthalicdialdehyde; pure isomers could only be obtained by tedious separation: [26a] H. Heimgartner, L. Ulrich, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1971, 54, 2313-2354.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.