A Strain Induced Change of Mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] Cycloaddition Reaction | Zendy

AnneFlorence TranVan | Zendy; Silas Götz | Zendy; Markus Neuburger | Zendy; Hermann A. Wegner | Zendy

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A Strain Induced Change of Mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] Cycloaddition Reaction

Author(s) -

AnneFlorence TranVan,

Silas Götz,

Markus Neuburger,

Hermann A. Wegner

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5007604

Subject(s) - cycloaddition , chemistry , cyclobutadiene , terphenyl , strain (injury) , mechanism (biology) , catalysis , ethylene , ring strain , ethylene glycol , molecule , computational chemistry , stereochemistry , combinatorial chemistry , organic chemistry , epistemology , medicine , philosophy

While investigating the [2 + 2 + 2] cycloaddition as a tool to build up strained oligophenyl systems with a diyne-ethylene glycol macrocyle, a surprising change of mechanism was observed. Instead of the expected [2 + 2 + 2] para-terphenyl, the ortho-terphenyl product explained by a formal [2 + 1 + 2 + 1] cycloaddition was formed. An η(4)-coordinated metal-cyclobutadiene is proposed as the key structure in the catalytic cycle, which is formed to release the induced strain. The optical properties of the ortho-terphenyl products have been measured as well as the coordination ability of Na(+) and K(+).

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