{{Short description|Chemical reaction}} A '''dearomatization reaction''' is an organic reaction in which the reactants are arenes and the products permanently lose their aromaticity.<ref name=pigge2015 /> It is of some importance in synthetic organic chemistry for the organic synthesis of new building blocks <ref name=pigge2015 /> and in total synthesis.<ref name=roche2011 /> Types of carbocyclic arene dearomization include hydrogenative (Birch reduction), alkylative, photochemical, thermal, oxidative, transition metal-assisted and enzymatic.<ref name=pigge2015 />
==Photochemical== Examples of photochemical reactions are those between certain arenes and alkenes forming [2+2] and [2+4] cycloaddition adducts.<ref name=pigge2015 />
==Enzymatic== {{Main|Microbial arene oxidation}} Examples of enzymes capable of arene dearomatization <ref name=boll2014 /><ref name=boll2005 /> are toluene dixoyhydrogenase, naphthalene dixoyhydrogenase and benzoyl CoA reductase.<ref name=pigge2015 />
==Transition metal-assisted== A classic example of transition metal-assisted dearomatization is the Buchner ring expansion.<ref name=pigge2015 /> Catalytic asymmetric dearomatization reactions (CADA) are used in enantioselective synthesis.<ref name=zhang2012 />
==References== {{reflist|colwidth=50em |refs= <ref name=pigge2015>Pigge, F. C. (2015) ''Dearomatization Reactions, in Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds'' (ed J. Mortier), John Wiley & Sons, Inc, Hoboken, NJ. {{doi|10.1002/9781118754887.ch15}}</ref> <ref name=roche2011>Roche, S. P. and Porco, J. A. (2011), ''Dearomatization Strategies in the Synthesis of Complex Natural Products.'' Angew. Chem. Int. Ed., 50: 4068–4093. {{doi|10.1002/anie.201006017}}</ref> <ref name=boll2005>''Dearomatizing Benzene Ring Reductases'' Boll M. J Mol Microbiol Biotechnol 2005;10:132–142 {{doi|10.1159/000091560}}</ref> <ref name=boll2014>''Anaerobic degradation of homocyclic aromatic compounds via arylcarboxyl-coenzyme A esters: organisms, strategies and key enzymes''. Boll M, Löffler C, Morris BE, Kung JW. Environ Microbiol. 2014 Mar;16(3):612-27. {{doi|10.1111/1462-2920.12328}}</ref> <ref name=zhang2012>Zhuo, C.-X., Zhang, W. and You, S.-L. (2012), ''Catalytic Asymmetric Dearomatization Reactions''. Angew. Chem. Int. Ed., 51: 12662–12686. {{doi|10.1002/anie.201204822}}</ref> }}
Category:Organic reactions