[3+2] Cycloadditions: Part XXXV. Selective Cycloadditions of C-(4-Chlorophenyl)-N-methyl Nitrone to Cinnamic Acid Anilides

Methyl N-(4-chlorophenyl)succinamate

In the structure of the title compound {systematic name: methyl 3-[(4-chloro-phen-yl)amino-carbon-yl]propionate}, C(11)H(12)ClNO(3), the conformations of the N-H and C=O bonds in the amide fragment are trans to each other and the conformations of the amide O atom and the carbonyl O atom of the ester fragment are also trans to the H atoms attached to the adjacent C atoms. Mol-ecules are linked i...

Theoretical study of 1, 3-dipolar cycloadditions of nitrone and fulminic acid with substituted ethylenes

[2n2π + 2n2π] cycloadditions: an alternative to forbidden [4π + 4π] processes. The case of nitrone dimerization.

A theoretical study based on (U)M06-2X/cc-pVTZ calculations has been used to investigate the [3 + 3] thermal dimerization of nitrones to 1,4,2,5-dioxadiazinanes in both the gas phase and in dichloromethane solution. Calculations suggest that dimerization of nitrones takes place through a concerted mechanism involving a formal disallowed [4π + 4π] cycloaddition with a free energy barrier of 30.8...

Mild arylboronic acid catalyzed selective [4 + 3] cycloadditions: access to cyclohepta[b]benzofurans and cyclohepta[b]indoles.

The first example of arylboronic acid catalyzed [4 + 3] cycloaddition reaction is reported. 3,5-Bis-(trifluoromethyl) phenylboronic acid is shown to be the best catalyst in this reaction. The method has also enabled the preparation of cyclohepta[b]benzofurans and cyclohepta[b]indoles in excellent yields.

Selective Halogen-Lithium Exchange of 1,2-Dihaloarenes for Successive [2+4] Cycloadditions of Arynes and Isobenzofurans.

Successive [2+4] cycloadditions of arynes and isobenzofurans by site-selective halogen-lithium exchange of 1,2-dihaloarenes were developed, allowing the rapid construction of polycyclic compounds which serve as a useful synthetic intermediates for the preparation of various polyacene derivatives.