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Volumn 44, Issue 3, 2012, Pages 372-376

Convenient synthesis of ethenylcyclopropane and some 2- cyclopropylcyclopropane derivatives

Author keywords

alkenes; bromination; cyclopropanation; elimination; reduction; small rings

Indexed keywords

BORONATE; BROMINATION; CURTIUS DEGRADATION; CYCLOPROPANATION; CYCLOPROPYL; DIIODOMETHANE; ELIMINATION; ETHYL DIAZOACETATE; METHYL KETONES; REDUCTIVE ELIMINATION; SMALL RINGS; TRANS-ISOMERS;

EID: 84856227875     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289600     Document Type: Article
Times cited : (4)

References (52)
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    • For one of us (A. d. M.), this is considered to be Part 160 in the series Cyclopropyl Building Blocks for Organic Synthesis. Part 159: http://www.beilstein-journals.org/bjoc
    • For one of us (A. d. M.), this is considered to be Part 160 in the series Cyclopropyl Building Blocks for Organic Synthesis. Part 159:, Kozhushkov S I., Khlebnikov A F., Kostikov R R., Yufit D S., deMeijere A, Beilstein J. Org. Chem. 2011 7 1003; http://www.beilstein-journals.org/bjoc
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    • 2-Cyclopropylcyclopropanamine has been mentioned as a component of certain benzamides in a number of patents, but no procedure for its preparation has been published. See, e.g. WO 2009111553 A1; 2009, 151, 313544 WO 2009085816 A1 2009; Chem. Abstr. 2009, 151, 123984 WO 2009061991 A1 2009; Chem. Abstr. 2009, 150, 539706 WO 2009006061 A2 2009; Chem. Abstr. 2009, 150, 121640 WO 2008082502 A2 2008; Chem. Abstr. 2009, 149, 152831
    • 2-Cyclopropylcyclopropanamine has been mentioned as a component of certain benzamides in a number of patents, but no procedure for its preparation has been published. See, e.g., Dumas D J., WO 2009111553 A1 2009; Chem. Abstr. 2009, 151, 313544, Dumas D J., Casalnuovo A, WO 2009085816 A1 2009; Chem. Abstr. 2009, 151, 123984, Grushin V, Casalnuovo A, WO 2009061991 A1 2009; Chem. Abstr. 2009, 150, 539706, Annis G D., WO 2009006061 A2 2009; Chem. Abstr. 2009, 150, 121640, Annis G D., Bruening J, Currie M J., Dumas D J., Shapiro R, WO 2008082502 A2 2008; Chem. Abstr. 2009, 149, 152831
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    • The bromo ketone 2 and the bromohydrin 3 have previously been prepared, but no experimental details have been reported: Angew. Chem. 1985, 97, 1074
    • The bromo ketone 2 and the bromohydrin 3 have previously been prepared, but no experimental details have been reported:, Pirrung M C., McGeehan G M., Angew. Chem., Int. Ed. Engl. 1985 24 1044; Angew. Chem. 1985, 97, 1074
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    • For examples of rapid (cyclopropylcarbinyl)metal-to-(homoallyl)metal rearrangements, see
    • For examples of rapid (cyclopropylcarbinyl)metal-to-(homoallyl)metal rearrangements, see:, Zhao L, deMeijere A, Adv. Synth. Catal. 2006 348 2484
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    • Zhao, L.1    Demeijere, A.2


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