Quaternary carbon

Short description: A carbon atom bound to four other carbon atoms

quaternary carbon

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Structural formula of neopentane (quaternary carbon is highlighted red)

A quaternary carbon is a carbon atom bound to four other carbon atoms.[1] 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.[2]

| primary carbon | secondary carbon | tertiary carbon | quaternary carbon

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General structure
(R = Organyl group)  |  |  |  |
Partial
Structural formula |  |  |  |

## 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,[3] Heck reaction, Enyne cyclization, cycloaddition reactions,[4] C–H activation, Allylic substitution,[5] Pauson–Khand reaction,[6] 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" (in en) (Book). Organic chemistry (3rd ed.). New York, NY: McGraw-Hill. p. 116. ISBN 978-0-07-337562-5. http://highered.mheducation.com/sites/007340277x/student_view0/index.html. Retrieved 2018-06-26.
2. ↑ Hans Peter Latscha, Uli Kazmaier, Helmut Alfons Klein (2016) (in German), Organische Chemie: Chemie-Basiswissen II (7. Auflage ed.), Berlin: Springer Spektrum, p. 40, ISBN 978-3-662-46180-8
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. ↑ "Allylic Substitution for Construction of a Chiral Quaternary Carbon Possessing an Aryl Group". J. Org. Chem. 78 (8): 3755–3766. 2013. 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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