Pathways of reactions of 2-arylcyclopropane-1,1-dicarboxylates with monosubstituted cycloheptatrienes under the action of GaCl3

Pathways of reactions of 2-arylcyclopropane-1,1-dicarboxylates with monosubstituted cycloheptatrienes under the action of GaCl3 Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 5, Pages: 1229-1236 Pages count : 8 DOI: 10.1007/s11172-024-4239-1

Authors

Borisov D.D. ¹ , Ershova A.A. ¹ , Platonov D.N. ¹ , Novikov R.A. ¹ , Tomilov Yu.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The reaction of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) with the unsaturated cyclohepta-2,4,6-triene-1-carboxylate system under the action of GaCl3 proceeds with a contraction of the seven-membered cycle and formally corresponds to the [2+4] or [3+2] cycloaddition of 1,2- or 1,3-zwitterionic intermediates generated from ACDCs to the double bonds of the norcaradiene structure. On the contrary, cycloheptatrienes with donor substituents practically do not form cycloaddition products in reactions with 1,2-zwitterionic intermediates, but undergo dehydrogenation and significant oligomerization. Methyl- and phenylcycloheptatriene turned out to be rather good precursors of hydride ions, which resulted in the formation of (2-phenylethyl)malonate, while 7-methoxycycloheptatriene predominantly transforms the 1,2-zwitterion open form to the initial ACDC.

Borisov D.D. , Ershova A.A. , Platonov D.N. , Novikov R.A. , Tomilov Y.V.
Pathways of reactions of 2-arylcyclopropane-1,1-dicarboxylates with monosubstituted cycloheptatrienes under the action of GaCl3
Russian Chemical Bulletin. 2024. V.73. N5. P.1229-1236. DOI: 10.1007/s11172-024-4239-1 WOS Scopus OpenAlex

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