Unexpected Lewis Acid-Mediated Dimerization of 1,3-Diarylpropargylic Alcohols

Feng, An-Hsuan; Chen, Jyh-Yang; Yang, Lian‐Ming; Lee, Gene‐Hsiang; Wang, Yu; Luh, Tien‐Yau

doi:10.1021/jo015882e

Cited by 8 publications

(2 citation statements)

References 29 publications

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“…Acid-catalysed dimerization of 1,3-diarylpropargyls to afford diallenes has been reported. [30] Also, radical and carbenoid mechanisms have been invoked to explain the formation of propargylallenes from bromoallenes. [27,28] In our case the formation of F occurs without any catalysis and a pure radical mechanism (already proposed by McGlinchey and co-workers for the formation of some dimers of bromoallene) can be envisaged.…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

et al. 2011

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International audienceHerein we describe the synthesis of new substituted tetraaryltetracenes, obtained by the dimerization of triarylchloroallenes, prepared from propargyl alcohols. The propargyl alcohols were prepared by two different synthetic strategies and then the alcohols were treated to obtain the corresponding acenes. In addition to the expected tetracene derivatives, we observed the formation of bis(alkylidene)cyclobutenes. When strong electron-donating substituents were present, the main product was the cyclobutene. We discuss a reaction mechanism that accounts for the formation of the cyclobutenes

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Section: Mechanistic Considerationsmentioning

confidence: 99%

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

et al. 2011

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“…It is also possible to obtain 14 directly from 5 by Lewis acid mediated dimerization. 28 Therefore, we assume that the precursor of 14 are both compounds that underwent reaction according to the proposed mechanism (Scheme 4). We decided to look closer at the 13 C NMR spectra of allenes 10 and 13 (see Figure 1).…”

Section: Methodsmentioning

confidence: 99%