Myers-Saito cyclization

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The Myers-Saito cyclization , Myers-Saito reaction or also called Myers rearrangement , is a name reaction in organic chemistry that goes back to the chemists Andrew G. Myers and Isao Saito. The reaction was first published in 1989 as an intermolecular rearrangement of enynallenes .

Overview reaction

In the Myers-Saito cyclization z. B. cis -1,2,4-heptatriene-6-yne ( 1 ) rearranged to toluene ( 2 ).

Overview reaction of the Myers – Saito cyclization

This reaction principle can be transferred to derivatives of cis -1,2,4-heptatriene-6-yne.

Reaction mechanism

A possible reaction mechanism for the Myers - Saito cyclization is described by Zerong Wang as follows:

Proposed reaction mechanism for the Myers – Saito cyclization

The cis -1,2,4-heptatriene-6-yne ( 1 ) forms the 1-phenylmethyldiradical ( 2 ) through an intermolecular rearrangement . The 1,4-cyclohexadiene serves as a proton supplier and protonates the diradical to the product toluene ( 3 ).

application

The Myers-Saito cyclization is used in preparative chemistry for the synthesis of polycyclic aromatic ring systems .

See also

Bergman cyclization and Schmittel cyclization

Individual evidence

  1. ↑ a b c d e Zerong Wang: Comprehensive Organic Name Reactions and Reagents, Volume 2 . John Wiley, Hoboken (NJ) 2009, ISBN 978-0-470-28662-3 , pp. 2003-2006 .
  2. ↑ BP Mundy, MG Ellerd and FG Favaloro Jr. (ed.): Name Reactions and Reagents in Organic Synthesis, Secound Edition . John Wiley & Sons, Hoboken, NJ 2005, ISBN 0-471-22854-0 , p. 444.