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Volumn , Issue 9, 2009, Pages 1477-1484

Synthesis of cyclopropenes via 1,2-elimination of bromocyclopropanes catalyzed by crown ether

Author keywords

Amides; Crown ether; Cyclopropenes; Eliminations; Phase transfer catalysis

Indexed keywords

18-CROWN-6; CARBOXAMIDES; CATALYTIC AMOUNTS; CYCLOPROPENE; CYCLOPROPENES; EFFICIENT SYNTHESIS; ELIMINATIONS; ETHEREAL SOLVENTS; FUNCTIONALIZED; PHASE-TRANSFER CATALYSIS; SYNTHETIC PROTOCOLS;

EID: 66249147930     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088122     Document Type: Article
Times cited : (27)

References (72)
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    • For additions of C-H entities, see: (n) Sherrill, W. M.; Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804.
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    • For other transformations, see: p
    • For other transformations, see: (p) Rubina, M.; Woodward, E. W.; Rubin, M. Org. Lett. 2007, 9, 5501.
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    • For recent applications of cyclopropenes in organic synthesis, see, for example
    • For recent applications of cyclopropenes in organic synthesis, see, for example: Pallerla, M. K.; Fox, J. M. Org. Lett. 2007, 9, 5625.
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    • For leading references on catalytic asymmetric cyclopropenations, see: d
    • For leading references on catalytic asymmetric cyclopropenations, see: (d) Doyle, M. P.; Protopopova, M.; Muller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
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    • (h) See ref. 2v.
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    • and references cited therein. See, for example
    • See, for example: Sherrill, W. M.; Kim, R.; Rubin, M. Tetrahedron 2008, 64, 8610; and references cited therein.
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    • For applications of cyclopropene-3-carboxamides in organic, bioorganic, and organometallic chemistry, see: a
    • For applications of cyclopropene-3-carboxamides in organic, bioorganic, and organometallic chemistry, see: (a) Yan, N.; Liu, X.; Pallerla, M. K.; Fox, J. M. J. Org. Chem. 2008, 73, 4283.
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    • On facile base-assisted alcoholysis of N,N-diarylamides, see, for example: (a) Ulbrich, H. K.; Luxenburger, A.; Prech, P.; Eriksson, E. E.; Soehnlein, O.; Rotzius, P.; Lindbom, L.; Dannhardt, G. J. Med. Chem. 2006, 49, 5988.
    • On facile base-assisted alcoholysis of N,N-diarylamides, see, for example: (a) Ulbrich, H. K.; Luxenburger, A.; Prech, P.; Eriksson, E. E.; Soehnlein, O.; Rotzius, P.; Lindbom, L.; Dannhardt, G. J. Med. Chem. 2006, 49, 5988.
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    • Side product 9, once formed, rapidly decomposed under the reaction conditions. Low stability of cyclopropene-3-carboxylic esters toward nucleophilic attack by potassium tert-butoxide was previously reported, see: Kudrevich, S. V.; Rubin, M. A.; Tarabaeva, O. G.; Surmina, L. S.; Baird, M. S.; Bolesov, I. G. Zh. Org. Khim. 1994, 30, 945.
    • Side product 9, once formed, rapidly decomposed under the reaction conditions. Low stability of cyclopropene-3-carboxylic esters toward nucleophilic attack by potassium tert-butoxide was previously reported, see: Kudrevich, S. V.; Rubin, M. A.; Tarabaeva, O. G.; Surmina, L. S.; Baird, M. S.; Bolesov, I. G. Zh. Org. Khim. 1994, 30, 945.
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    • While all the cyclopropenes used in this work have a methyl group at C3, there is no indication that the presented synthetic method is limited to this particular type of substrate. Those reported here were chosen for these studies because they were the most readily available model compounds
    • While all the cyclopropenes used in this work have a methyl group at C3, there is no indication that the presented synthetic method is limited to this particular type of substrate. Those reported here were chosen for these studies because they were the most readily available model compounds.


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