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Stereoconvergent Generation of a Contrasteric syn-Bicyclopropylidene (=syn-Cyclopropylidenecyclopropane) by Stille-Like Coupling
Date
2013-05-01
Author
GÜNEY, MURAT
Essiz, Selcuk
DAŞTAN, Arif
Balcı, Metin
De Lucchi, Ottorino
ŞAHİN, Ertan
Fabris, Fabrizio
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Stereoisomerically pure endo- and exo-7-halo-7-(trimethylstannyl)benzonorcar-3-enes (=endo- and exo-(1-halo-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-1-yl)trimethylstannane) 4 and 6 were selectively obtained by lithiumtin or magnesiumtin transmetalation in good yields (Scheme2 and 3). The reaction of these compounds with copper(I) thiophene-2-carboxylate (CuTC) produced in both cases the corresponding CS-symmetric bicyclopropylidene (=cyclopropylidenecyclopropane) syn-1, a single diastereoisomer (Schemes5 and 6). The structure of syn-1 was undoubtedly elucidated by X-ray single crystal diffraction. The coupling mechanism of the carbenoid cyclopropane is discussed (Scheme7).
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
,
Biochemistry
,
Drug Discovery
,
Catalysis
URI
https://hdl.handle.net/11511/57514
Journal
HELVETICA CHIMICA ACTA
DOI
https://doi.org/10.1002/hlca.201200291
Collections
Graduate School of Natural and Applied Sciences, Article
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BibTeX
M. GÜNEY et al., “Stereoconvergent Generation of a Contrasteric syn-Bicyclopropylidene (=syn-Cyclopropylidenecyclopropane) by Stille-Like Coupling,”
HELVETICA CHIMICA ACTA
, vol. 96, no. 5, pp. 941–950, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57514.