64884-88-4Relevant 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.
Formation of homoallyl alcohols and 4-chlorotetrahydropyrans from allyl-stannanes, aldehydes and TiCl4 or Cp2TiCl2
Marton, Daniele,Tagliavini, Giuseppe,Zordan, Michele,Wardell, James L.
, p. 295 - 305 (2007/10/02)
Reaction between Bu3SnCHR1CH=CHR2 (1; R1 = H, R2 = H or Me; R1, R2 = (CH2)3) and EtCHO in the presence of TiCl4 or Cp2TiCl2 are reported.The compound, Cp2TiCl2, has been found to be an effective Lewis acid catalyst for the allylation of EtCHO using 1 (R1 = H, R2 = Me) and 1 (R1, R2 = (CH2)3) in CH2Cl2 or Et2O solutions at -78 deg C; the products after hydrolysis are homoallyl alcohols with stereo- and regio-selectivities different from those found for TiCl4- reactions.Reactions with an excess of EtCHO in the presence of TiCl4 give 4-Cl-3-R1-5-R2-2,6-2Et-tetrahydropyrans (2) via insertions of a second EtCHO into the metal-O bond of the initially produced homoallyl alcoholate: the trans-2 compounds are obtained from threo-EtCH(OM')CHR2CH=CHR1 and cis-2 from erythro-EtCH(OM')CHR2CH=CHR1 (e.g., M' = TiCl3).
ALLYLSTANNATION. XI. A NEW CONVENIENT METHOD FOR THE SYNTHESIS OF 9-CHLORO-2,4-DIETHYL-cis-3-OXABICYCLONONANE
Marton, Daniele,Furlani, Donatella,Tagliavini, Giuseppe
, p. 189 - 190 (2007/10/02)
trans and cis-9-chloro-2,4-diethyl-cis-3-oxabicyclononane in the ratio 75:25 can be prepared via allylstannation by reacting cyclohex-2-enylbutyltin dichloride with propionaldehyde.