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Volumn 7, Issue 18, 2001, Pages 4021-4034

Spirocyclopropanated bicyclopropylidenes: Straightforward preparation, physical properties, and chemical transformations

Author keywords

Bicyclopropylidene; Carbenoids; Cyclopropanation; Small ring systems; Strained molecules

Indexed keywords

BROMINE; CRYSTAL STRUCTURE; HYDROCARBONS; HYDROGENATION; STRUCTURAL ANALYSIS; SYNTHESIS (CHEMICAL);

EID: 0035903606     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010917)7:18<4021::AID-CHEM4021>3.0.CO;2-E     Document Type: Article
Times cited : (36)

References (111)
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    • note
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    • For comparison, in spiropentane itself the angles ψ and Φ are 90.2° and 179.6° respectively, while in ethano-bridged spiropentane ψ and Φ are 80.0° and 154.0° respectively. Compare: R. Boese, D. Bläser, K. Gomann, U. H. Brinker, J. Am. Chem. Soc. 1989, 111, 1501-1503.
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    • The unsubstituted bicyclo[2.2.0]hex-1(4)ene has been found to be a highly reactive alkene: a) J. Casanova, H. R. Rogers, J. Org. Chem. 1974, 39, 3803;
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    • The cyclopropylcyclopropylidene to bicyclo[2.1.0]pent-1(4)-ene rearrangement followed by ring opening to an alkylidenecyclobutylidene involved in this mechanism may actually play a general role in the so far unexplained formation of various cyclobutene derivatives upon treatment of dihalotriangulanes with alkyllithium reagents. See refs. [5a,b,7b] and: a) K. A. Lukin, N. S. Zefirov, D. S. Yufit, Yu. T. Struchkov, Tetrahedron 1992, 48, 9977-9984;
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    • note
    • For a discussion of interrelations between strain and stability in higher polyspirocyclopropane aggregates as well as possible carbon networks of spirocyclopropane units see ref. [5a].
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    • For the most successful examples of such transformations see: a) B. Rissom, L. Fitjer, Tetrahedron 1997, 53, 7529-7538;
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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-155472 [(E)-14], -142835 (17), -155473 (20), -142836 (32), -142041 (33), -155474 (36), -155475 (37), -155476 (38), -142837 (51). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.