40391-19-3Relevant articles and documents
The formation of 7-oxabicyclo[4.2.0]octanes and 6-oxabicyclo[3.2.1]octanes via cationic iodocyclization
Nichols, Christopher J.
, p. 2167 - 2179 (2007/10/03)
Several 2-cyclohexenemethanol derivatives were subjected to cationic iodocyclization. Two product types were formed: the fused 7-oxabicyclo[4.2.0]octane, and the bridged 6-oxabicyclo[3.2.1]octane. The degree of substitution in the alkenol determined the ratio of the products, with aromatic substituents leading to the formation of the fused system as the major product.
Hydrated ?-bonded organometallic cations in organic synthesis. I. Allyl-, crotyl-, 1-methylallyl-, cyclohex-2-enyl-, and cinnamyl-stannation of carbonyl compounds in water
Furlani, Donatella,Marton, Daniele,Tagliavini, Giuseppe,Zordan, Michele
, p. 345 - 356 (2007/10/02)
Homoallylic alcohols can be prepared in water by allyl-, crotyl-, 1-methylallyl-, cyclohex-2-enyl-, or cinnamyl-stannation of such carbonyl compounds as aldehydes, dialdehydes, and ketones, as well as acetals.The procedure is based on: Bu2RSnCl + R'COR" + (1/2)H2O -> R(HO)CR'R" + (1/2)(Bu2SnCl)2O where R = allyl, crotyl, 1-methylallyl, cyclohex-2-enyl, or cinnamyl group, R' = H or alkyl group, R" R'= alkyl group.In most cases, the reaction products are obtained rapidly in high yields (80-100percent).Hydrated organometallic cations Bu2RSn+(aq) are partly involved.These results, together with those already published on 2-propynyl-and allenyl-stannation, indicate the value of this procedure.
Hydroboration. 76. Hydroboration of Cyclic Dienes with Representative Hydroborating Agents
Brown, Herbert C.,Bhat, Krishna S.
, p. 445 - 449 (2007/10/02)
A detailed study was made of the hydroboration of cyclic dienes with representative hydroborating agents: borane-methyl sulfide (BMS), 9-borabicyclononane (9-BBN), disiamylborane (Sia2BH), dibromo-borane-methyl sulfide (Br2BH*SMe2), and dibromoborane (Br2BH). 1,4-Cyclohexadiene essentially undergoes monohydroboration with a stoichiometric amount of the representative hydroborating agents, whereas 1,5-cyclooctadiene gives the dihydroboration product predominantly.The rapid dimerization of 1,3-cyclopentadiene introduces a complication into its hydroboration.However, monomeric cyclopentadiene undergoes hydroboration primarily to the homoallylic derivative with little of the desired allylic product.Hydroboration of 1,3-cyclohexadiene with a stoichiometric amount of the hydroborating agent furnishes mainly the allylboranes, which upon treatment with acetaldehyde followed by oxidation, furnishes 1-(2-cyclohexenyl)-1-ethanol in good yield.Similary, hydroboration of 1,3-cycloheptadiene and 1,3-cyclooctadiene furnished dihydroborated products preferentially, with lower yields of the corresponding allylboranes, characterized as 1-(2-cycloheptenyl)-1-ethanol and 1-(2-cyclooctenyl)-1-ethanol, respectively, following reaction with acetaldehyde.