《Electrochemical-Induced Ring Transformation of Cyclic α-(ortho-Iodophenyl)-β-oxoesters》 was published in Chemistry – A European Journal in 2020. These research results belong to Strehl, Julia; Kahrs, Christoph; Mueller, Thomas; Hilt, Gerhard; Christoffers, Jens. Electric Literature of C7H12O3 The article mentions the following:
Cyclic α-(ortho-iodophenyl)-β-oxoesters R3-2-IC6H3CH(R2)(C(O)OR)C(O)R1 (R = Me, Et; R1 = Me, Ph; R2 = H, Me; R1R2 = -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-; R3 = 2-Me, 3-Br, 4-methoxycarbonyl, etc.) and Me 2-(2-iodophenyl)-1-oxoindane-2-carboxylate, Et 2-(2-iodophenyl)-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate were converted in a ring-expanding transformation to furnish benzannulated cycloalkanone carboxylic esters R3-2-R1C(O)C6H3CH(R2)C(O)OR and Et 12-oxo-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctadiene-5-carboxylate. The reaction sequence started by electrochem. reduction of the iodoarene moiety. In a mechanistic rationale, the resulting carbanionic species was added to the carbonyl group under formation of a strained, tricyclic benzocyclobutene intermediate, which underwent carbon-carbon bond cleavage and rearrangement of the carbon skeleton by retro-aldol reaction. The scope of the reaction sequence was investigated by converting cyclic oxoesters with different ring sizes yielding benzocycloheptanone, -nonanone and -decanone derivatives in moderate to good yields. Furthermore, acyclic starting materials and cyclic compounds carrying addnl. substituents on the iodophenyl ring were submitted to this reaction sequence. The starting materials for this transformation are straightforwardly obtained by conversion of β-oxoesters R1C(O)CH(R2)C(O)OR with phenyliodobis(trifluoroacetate) R3C6H4I((O)OCCF3)2. In addition to this study using Ethyl 2-methyl-3-oxobutanoate, there are many other studies that have used Ethyl 2-methyl-3-oxobutanoate(cas: 609-14-3Electric Literature of C7H12O3) was used in this study.
Ethyl 2-methyl-3-oxobutanoate(cas: 609-14-3) belongs to ketone compounds. Ketones are highly reactive, although less so than aldehydes, to which they are closely related. Much of their chemical activity results from the nature of the carbonyl group. Ketones readily undergo a wide variety of chemical reactions.Electric Literature of C7H12O3
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