Quaternary carbon explained

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.

Synthesis

The formation of chiral quaternary carbon centers has been a synthetic challenge. Chemists have developed asymmetric Diels–Alder reactions,^[2] Heck reaction, Enyne cyclization, cycloaddition reactions,^[3] C–H activation, Allylic substitution,^[4] Pauson–Khand reaction,^[5] etc. to construct asymmetric quaternary carbon atoms.

References

1. Book: Smith . Janice Gorzynski . Hodge . Tami . Nemmers . Donna . Klein . Jayne--> . Organic chemistry . 2011 . McGraw-Hill . New York, NY . 978-0-07-337562-5 . 116 . 3rd . en . Book . Chapter 4 Alkanes . 2018-06-26 . https://web.archive.org/web/20180628152511/http://highered.mheducation.com/sites/007340277x/student_view0/index.html . 2018-06-28 . dead .
2. Nicolaou, K. C.; Vassilikogiannakis, G.; Mägerlein, W.; Kranich, R Angew. Chem. Int. Ed. Volume 2001, Issue 40, Pages 2482–2486
3. Quasdorf, K.W.; Overman, L. E. Nature Volume 2014, Volume 516, Pages 181
4. Feng C, Kobayashi Y . Allylic Substitution for Construction of a Chiral Quaternary Carbon Possessing an Aryl Group. J. Org. Chem.. 2013. 78. 8. 3755–3766. 10.1021/jo400248y. 23496084.
5. Ishizaki, M.; Niimi, Y.; Hoshino, O.; Hara, H.; Takahashi, T. Tetrahedron Volume 2001, Issue 61, Pages 4053–4065