Editing Quinone (section)

=== Addition ===
Quinones undergo addition reaction to form 1,4-addition products.<ref name=":0">{{Citation |last1=Smith |first1=P. W. G. |date=1969-01-01 |url=https://www.sciencedirect.com/science/article/pii/B9780080129488500103 |work=Aromatic Chemistry |pages=144–175 |editor-last=Smith |editor-first=P. W. G. |publisher=Pergamon |language=en |doi=10.1016/b978-0-08-012948-8.50010-3 |isbn=978-0-08-012948-8 |access-date=2022-11-17 |last2=Tatchell |first2=A. R. |title=Aromatic Alcohols and Carbonyl Compounds |editor2-last=Tatchell |editor2-first=A. R.|url-access=subscription }}</ref> An example of 1,4-addition reaction is the addition of [[hydrogen chloride]] to form chlorohydroquinone:  
[[File:QuinoneAdditionReaction.png|center|thumb|class=skin-invert-image|240x240px|1,4-addition reaction of quinone with hydrogen chloride to produce chlorohydroquinone]]
Quinones can undergo [[Diels–Alder reaction|Diels–Alder reactions]].<ref name=":0" /> The quinone acts as the dienophile and reacts with a diene at a carbon-carbon double bond.

In [[Diels–Alder reaction]]s quinones are used as dienophiles. Historically important [[total synthesis|syntheses]] include [[cholesterol total synthesis|cholesterol]], [[cortisone]], [[total synthesis of morphine and related alkaloids|morphine]], and [[reserpine]].<ref>{{Cite journal |last1=Nawrat |first1=Christopher C. |last2=Moody |first2=Christopher J. |date=2014-02-17 |title=Quinones as Dienophiles in the Diels–Alder Reaction: History and Applications in Total Synthesis |url=https://onlinelibrary.wiley.com/doi/10.1002/anie.201305908 |journal=Angewandte Chemie International Edition |language=en |volume=53 |issue=8 |pages=2056–2077 |doi=10.1002/anie.201305908|pmid=24446164 |s2cid=1362687 }}</ref>