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Stereochemical specificities of carbonyl compounds of the Δ3-cyclohexene series by G.P. Kugatova-Shemyakina; Yu.A. Ovchinnikov is a Chemistry article available to read on EtoBox.

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An explanation of the unique chemical behaviour of carbonyl compounds of the Aa-cyclohexene series is based on conformational theory. COMPOUNDS of the A3-cyclohexene series (aldehydes, ketones, ketols, acids and their derivatives) prepared by condensation of the corresponding dienes and dienophils, or by subsequent conversion of primary dienic condensation adducts, find wide application in the synthesis of certain types of natural products and their analogs. Compared with analogous cyclohexanic and A%yclohexenic derivatives the aforementioned compounds show a highly specific chemical behaviour. This can clearly be seen from the following: 1. The double bond of A3-cyclohexenic aldehydes (I) in contrast to that of acetals (II), secondary acetylenic alcohols (III) and other compounds of the same series has a greatly diminished reactivity, as evidenced, for instance, by the difficulty of its catalytic hydrogenation's2 and also follows from the relative inertness of the allylic bromine in some ally1 bromides of this species.3 2. The carbonyl group of AS-cyclohexenic aldehydes is also much less active than that of cyclohexanic or As-cyclohexenic aldehydes. This is clearly displayed in ox

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Author

G.P. Kugatova-Shemyakina; Yu.A. Ovchinnikov

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1962

Language

EN

Field

Chemistry (Physical Sciences)