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2.6.1.5 Method 5: Alkene Metathesis

DOI: 10.1055/sos-SD-002-00315

Poli, R.; Smith, K. M.Science of Synthesis, (20032290.

High-valent mo­lyb­de­numcarbene complexes bearing electronegative ancillary ligands are efficient catalysts for al­kene metathesis reactions (Scheme 8).[‌20‌,‌35‌] This reaction proceeds via [2+2] cy­clo­addition and formation of metalla­cy­clo­bu­tane intermediates, some of which have been isolated under controlled conditions (see Section 2.6.5.3).[‌36‌] In order to make the reaction synthetically useful, it is necessary to have a driving force and high selectivities, and to suppress the self-metathesis if a cross-metathesis (e.g., R1 R2) is desired. The driving force may be provided by conjugation or by formation of polymeric materials. Selective processes often result from the removal of a volatile byproduct, such as ethene.

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