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Quaternary carbon

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A carbon atom bound to four other carbon atoms
quaternary carbon
Structural formula of neopentane (quaternary carbon is highlighted red)

A quaternary carbon is a carbon atom bound to four other carbon atoms. For this reason, quaternary carbon atoms are found only in hydrocarbons having at least five carbon atoms. Quaternary carbon atoms can occur in branched alkanes, but not in linear alkanes.

primary carbon secondary carbon tertiary carbon quaternary carbon
General structure
(R = Organyl group) 		frameless=1.0 frameless=1.0 frameless=1.0 frameless=1.0
Partial
Structural formula 		frameless=1.0 frameless=1.0 frameless=1.0 frameless=1.0

Synthesis

Bis-Phenol A synthesis from acetone and phenol

The formation of chiral quaternary carbon centers has been a synthetic challenge. Chemists have developed asymmetric Diels–Alder reactions, Heck reaction, Enyne cyclization, cycloaddition reactions, C–H activation, Allylic substitution, Pauson–Khand reaction, etc. to construct asymmetric quaternary carbon atoms.

One of the most industrially important compounds containing a quaternary carbon is bis-phenol A (BPA). The central atom is a quaternary carbon. Retrosynthetically, that carbon is the central atom of an acetone molecule before condensation with two equivalents of phenol - BPA Production Process

References

  1. Smith, Janice Gorzynski (2011). "Chapter 4 Alkanes". Organic chemistry (3rd ed.). New York, NY: McGraw-Hill. p. 116. ISBN 978-0-07-337562-5. Archived from the original (Book) on 2018-06-28. Retrieved 2018-06-26.
  2. Hans Peter Latscha, Uli Kazmaier, Helmut Alfons Klein (2016), Organische Chemie: Chemie-Basiswissen II (in German) (7. Auflage ed.), Berlin: Springer Spektrum, p. 40, ISBN 978-3-662-46180-8{{citation}}: CS1 maint: multiple names: authors list (link)
  3. Nicolaou, K. C.; Vassilikogiannakis, G.; Mägerlein, W.; Kranich, R Angew. Chem. Int. Ed. Volume 2001, Issue 40, Pages 2482–2486 {{DOI: 10.1002/1521-3773(20010702)40:13<2482::AID-ANIE2482>3.0.CO;2-A}}
  4. Quasdorf, K.W.; Overman, L. E. Nature Volume 2014, Volume 516, Pages 181 {{doi:10.1038/nature14007}}
  5. Feng C, Kobayashi Y (2013). "Allylic Substitution for Construction of a Chiral Quaternary Carbon Possessing an Aryl Group". J. Org. Chem. 78 (8): 3755–3766. doi:10.1021/jo400248y. PMID 23496084.
  6. Ishizaki, M.; Niimi, Y.; Hoshino, O.; Hara, H.; Takahashi, T. Tetrahedron Volume 2001, Issue 61, Pages 4053–4065
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