Bridged bicyclic compounds, compared with

In addition, several bridged bicyclic compounds have been examined as potential substrates (Fig. 16.5-32). In contrast to the regiodivergent behaviour of the [n.2.0] bicyclic compounds, in these cases, only one lactone product is usually obtained. This high selectivity compares favorably with the chemical Baeyer-Villiger oxidation of compounds of this type, which often afford regiomixtures[U9). In addition, the... 

An hypothesis known as Bredt s Rule states that a double bond to a bridgehead of a smallring bridged bicyclic compound is not possible. The basis of this rule can be seen if you attempt to make a model of bicyclo[2.2.1 ]hept- 1-ene, A. One approach to the assembly of this model is to try to bridge the number 1 and number 4 carbon atoms of cyclohexene with a methylene (CH2) unit. Compare this bridging with the ease of installing a CH2 bridge... 

Although cyclizations from the direct anodic oxidation of acyclic 1,3-dicarbonyl compounds have not been reported, the analogous mediated reactions have been studied [24]. Snider and McCarthy compared oxidative cyclization reactions using a stoichiometric amount of Mn(OAc)3 with oxidations using a catalytic amount of Mn(OAc)3 that was recycled at an anode surface (Scheme 11). In the best case, the anodic oxidation procedure led to a 59% yield of the desired bridged bicyclic product with the use of only 0.2 equivalents (10% of the theoretical amount needed) of Mn(OAc)3- Evidence that the reaction was initiated by the presence of the mediator was obtained by examining the electrolysis reaction without the added Mn(OAc)3. In this case, none of the cyclized product was obtained. For comparison, the oxidation using... 

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