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A new bridge in [2.2]cyclophanes: The addition of Se2Cl2 to pseudogeminally substituted bispropargylic alcohols

✍ Scribed by M. Lucian Birsa; Henning Hopf

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 90 KB
Volume: 21
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20586

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✦ Synopsis

Abstract

The regio‐ and stereo‐specific addition of monoselenium monochloride to pseudogeminally substituted bispropargylic alcohols has been performed under high dilution conditions. The disproportionation reaction of selenium monochloride to selenium dichloride and triselenium dichloride leads to the corresponding divinylic mono‐ and tri‐selenides. The stereochemistry of the newly generated double bond was assigned as Z by 2D NMR experiments. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:126–130, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20586

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