This article is cited in 13 papers

Communications

Unexpected formation of substituted naphthalenes and phenanthrenes in a GaCl₃ mediated dimerization–fragmentation reaction of 2-arylcyclopropane-1,1-dicarboxylates

R. A. Novikov^a, A. V. Tarasova^a, K. Yu. Suponitsky^b, Yu. V. Tomilov<sup>a

a</sup> N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Dimethyl 2-arylcyclopropane-1,1-dicarboxylates on heating with GaCl₃ undergo dimerization to afford arylnaphthalenes or phenanthrenes. A possible reaction mechanism including elimination of two dimethyl malonate molecules was proposed, dimethyl malonate gallium complex Ga³⁺[H₂C(CO₂Me)₂]₃(GaCl^–) was isolated and characterized by X-ray diffraction analysis.

Language: English

DOI: 10.1016/j.mencom.2014.11.011

Bibliographic databases:

•