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Synthesis and Structure of a Strained, Cyclic meta ‐Quaterphenylene Acetylene
Author(s) -
De Hoe Clement,
Dean Ryan T.,
Hacker Allison S.,
Dutta Sudeep H.,
Dominguez Omar,
Parsons Leo W. T.,
Sommerville Parker J. W.,
Vandivier Kai P.,
Chalifoux Wesley A.,
Frantz Derik K.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900688
Subject(s) - chemistry , acetylene , alkyne , molecule , hydrocarbon , crystallography , annulene , yield (engineering) , carbon atom , solid state , stereochemistry , computational chemistry , organic chemistry , ring (chemistry) , materials science , metallurgy , catalysis
A strained, cyclic hydrocarbon comprising a meta ‐quaterphenyl‐based arc that is clamped by an alkyne tether was synthesized via Yamamoto coupling of a dichloro precursor. DFT calculations (B3LYP/6‐31G*) indicate that the lowest‐energy ground state adopts a twisted, C 2 conformation that bears 19.0 kcal/mol of strain energy. X‐ray crystallographic analysis confirms that, in the solid state, the molecule adopts a twisted structure that is similar to the calculated C 2 conformation. Exposure of the ortho ‐linked dichloro precursor to Yamamoto conditions generates 9,9′‐bisfluorenylidene in high yield.