Reactions of cyclooctatetraene dianion with aldehydes and ketones and the chemistry of its products

TS Cantrell, H Shechter

Index: Cantrell,T.S.; Shechter,H. Journal of the American Chemical Society, 1967 , vol. 89, # 23 p. 5877 - 5884

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Abstract

Abstract: Cyclooctatetraene dianion reacts as a 1, 2-and a 1, Cdicarbanionic reagent with benzaldehyde, acetaldehyde, o-phthalaldehyde, acetone, benzophenone, and fluorenone to give 5, 8-bis (a-hydroxyalkyl)-l, 3, 6-cyclooctatrienes, 7, 8-bis (cu-hydroxyalkyl) bicyclo [4.2. 0loctadienes, and 2, 4, 6, 8-tetraene-l, lO-diols. The bicyclo-[4.2. 0] octadienes and the 2, 4, 6, 8-tetraenediols are apparently formed by isomerization of the initial 7, 8- ...