80997-79-1Relevant articles and documents
Synthesis of η3-2-stannylmethylallylpalladium complexes and their destannylation leading to trimethylenemethane-palladium species
Watanabe, Saisuke,Ogoshi, Sensuke,Kakiuchi, Kiyomi,Kurosawa, Hideo
, p. 19 - 26 (1994)
η3-2-Stannylmethylallylpalladium chloride dimer 3-CH2C(CH2SnMe3)CH2)Cl>2 (1a) reacted with a neutral ligand L to form corresponding cationic complexes 3-CH2C(CH2SnMe3)CH2)L2>Cl (L=PPh3: 2a, 1/2 bipy: 5 (bipy=2,2'-bipyridyl)), which were characterized by 1H NMR at low temperature only for 2a and at room temperature for 5.On addition of Bu3SnCl the cationic complex 5 underwent stannyl group exchange equilibrium with 3-CH2C(CH2SnBu3)CH2) (bipy)>Cl.Addition of 2 equiv PPh3 and RCHO (R=Ph, CH2=CH) to 1a at room temperature afforded the cycloaddition products, methylenetetrahydrofurans, in good yields.The complex 1a reacted with PhCHO in the presence of bipy and dppe (dppe = 1,2-bis(diphenylphosphino)ethane) to give the aldehyde adduct complexes 3-CH2C(CH2CHPh(OSnMe3))CH2)L2>Cl (L=1/2 bipy, 1/2 dppe), which were characterized by 1H NMR.The possible generation and the reactivities of the trimethylenemethane-palladium complex intermediate are discussed in the light of these results.Key words: Palladium; Stannyl; Destannylation; Trimethylenemethane
Novel synthesis of methylenecyclobutanols and 4-methylenetetrahydrofurans from γ-oxide ylides
Okuma, Kentaro,Kamahori, Yoshihiro,Tsubakihara, Kimiko,Yoshihara, Kanami,Tanaka, Yuichiro,Shioji, Kosei
, p. 7355 - 7360 (2007/10/03)
The reaction of δ-halo-γ-oxide ylide, prepared from methylenetriphenylphosphorane and epichlorohydrin, with aldehydes afforded alkylidenecyclobutanols in moderate yields. The reaction initially proceeded through internal nucleophilic attack on δ-carbon of this ylide. Another novel approach toward the synthesis of 4-methylenetetrahydrofurans was achieved by the reaction of γ-oxide ylides with paraformaldehyde.
Tributyltin chloride-sodium cyanoborohydride mediated tandem radical cyclisation-reductive demethoxylation sequence
Srikrishna,Viswajanani,Yelamaggad
, p. 10479 - 10488 (2007/10/03)
Reaction of the bromoketals 3, 7a-g and 11 with tri-n-butyltin chloride and sodium cyanoborohydride in the presence of a catalytic amount of AIBN furnished the ethers 5, 8a-g and 13 via a tandem sequence comprising of a radical cyclisation reaction and tri-n-butylhalostannane and sodium cyanoborohydride mediated reductive demethoxylation of the resulting cyclic ketals.
