Molecules 2012, 17(12), 14531-14554; doi:10.3390/molecules171214531
Article

Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols

Michael Abraham 1 email, Wolfgang Reischl 1 email, Karl A. Kirchner 2 email, Alexander Roller 3 email, Luis F. Veiros 4 email and Michael Widhalm 1,* email
1 Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090 Wien, Austria 2 Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163/AC, A-1060 Wien, Austria 3 Faculty of Chemistry, Institute of Inorganic Chemistry, University of Vienna, Währinger Straße 42, A-1090 Wien, Austria 4 Centro de Química Estrutural, Instituto Superior Técnico, Universidade Técnica de Lisboa, 1049-001 Lisboa, Portugal
* Author to whom correspondence should be addressed.
Received: 30 October 2012; in revised form: 29 November 2012 / Accepted: 3 December 2012 / Published: 7 December 2012
(This article belongs to the Special Issue Claisen Rearrangement)
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Abstract: Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided.
Keywords: DFT calculations; Grubbs II catalyst; cage compounds; spiro-compounds; chiral macrocycle

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MDPI and ACS Style

Abraham, M.; Reischl, W.; Kirchner, K.A.; Roller, A.; Veiros, L.F.; Widhalm, M. Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols. Molecules 2012, 17, 14531-14554.

AMA Style

Abraham M, Reischl W, Kirchner KA, Roller A, Veiros LF, Widhalm M. Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols. Molecules. 2012; 17(12):14531-14554.

Chicago/Turabian Style

Abraham, Michael; Reischl, Wolfgang; Kirchner, Karl A.; Roller, Alexander; Veiros, Luis F.; Widhalm, Michael. 2012. "Tandem RCM–Claisen Rearrangement–[2+2] Cycloaddition of O,O'-(But-2-en-1,4-diyl)-bridged Binaphthols." Molecules 17, no. 12: 14531-14554.

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