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Volumn 5, Issue 5, 1999, Pages 1468-1473

B-alkylcatecholboranes as a source of radicals for efficient conjugate additions to unsaturated ketones and aldehydes

Author keywords

Boron; Cascade reactions; Domino reactions; Michael additions; Radical reactions

Indexed keywords

ALDEHYDE; BETA ALKYLCATECHOLBORANE; BORANE DERIVATIVE; BORON; KETONE; RADICAL; UNCLASSIFIED DRUG;

EID: 0032913898     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990503)5:5<1468::AID-CHEM1468>3.0.CO;2-7     Document Type: Article
Times cited : (66)

References (28)
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    • For review articles, see: H. C. Brown, M. M. Midland, Angew. Chem. 1972, 84, 702-710; Angew. Chem. Int. Ed. Engl. 1972, 11, 692-700; A. Ghosez, B. Giese, H. Zipse, In Methoden der Organische Chemie, Vol. E19a, 4th ed., Houben-Weyl, 1989, pp. 753-765.
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    • For review articles, see: H. C. Brown, M. M. Midland, Angew. Chem. 1972, 84, 702-710; Angew. Chem. Int. Ed. Engl. 1972, 11, 692-700; A. Ghosez, B. Giese, H. Zipse, In Methoden der Organische Chemie, Vol. E19a, 4th ed., Houben-Weyl, 1989, pp. 753-765.
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    • A related method based on the oxymercuration reaction has been reported: B. Giese, K. Heuck, Chem. Ber. 1979, 112, 3759-3765; B. Giese, K. Heuck, Tetrahedron Lett. 1980, 21, 1829-1832.
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    • A related method based on the oxymercuration reaction has been reported: B. Giese, K. Heuck, Chem. Ber. 1979, 112, 3759-3765; B. Giese, K. Heuck, Tetrahedron Lett. 1980, 21, 1829-1832.
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    • A method based on the conversion of symmetrical trialkylboranes into organomercury compounds has also been reported: B. Giese, G. Kretzschmar, Angew. Chem. 1981, 93, 1015-1016; Angew. Chem. Int. Ed. Engl. 1981, 20, 965-966.
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    • A method based on the conversion of symmetrical trialkylboranes into organomercury compounds has also been reported: B. Giese, G. Kretzschmar, Angew. Chem. 1981, 93, 1015-1016; Angew. Chem. Int. Ed. Engl. 1981, 20, 965-966.
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    • Alkyldiethylboranes, easily obtained by hydroboration with diethylborane (R. Köster, P. Binger, Inorganic Synthesis 1974, 15, 141-149), gave results similar to the ones obtained by Brown with compound 1. For instance, addition of cyclohexene to methyl vinyl ketone was achieved in 77% yield without addition of oxygen. However, when cyclohexenone was used as the radical trap, addition of oxygen was necessary and a 3:1 mixture resulting from the addition of cyclohexyl and ethyl radicals was observed.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.