[2 + 4] Cycloadditions of Tetramethylketenimmonium Ion to cis-fixed Dienes

Marchand-Brynaert, Jacqueline;Ghosez, Léon
(1974) Tetrahedron Letters — Vol. 4, p. 377-380 (1974)

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  • Marchand-Brynaert, JacquelineUCLouvain
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  • Ghosez, LéonUCLouvain
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Abstract
Me2C:C:N+Me2BF4- with RR1C:CHCH:CH2 (R = H, R1 = H, Me; R = Me, R1 = H) gave [2 + 2] cycloadducts, e.g. I, and with cyclopentadiene and 1,3-cyclohexadiene gave [2 + 4] cycloadducts, e.g. II. CH2:CMeCMe:CH2 reacted in both ways. The population of transoid and skew conformations in the dienes governed the mode of cycloaddn.
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Marchand-Brynaert, J., & Ghosez, L. (1974). [2 + 4] Cycloadditions of Tetramethylketenimmonium Ion to cis-fixed Dienes. Tetrahedron Letters, 4, 377-380. https://doi.org/10.1016/S0040-4039(01)82219-X (Original work published 1974)