38503-54-7Relevant academic research and scientific papers
Catalytic cross deoxygenative and dehydrogenative coupling of aldehydes and alkenes: A redox-neutral process to produce skipped dienes
Qian, Bo,Zhang, Guoying,Ding, Yongzheng,Huang, Hanmin
supporting information, p. 9839 - 9841 (2013/10/21)
A novel catalytic cross deoxygenative and dehydrogenative coupling reaction of aldehydes and alkenes was established via a cooperative catalysis approach. This transformation provided an efficient and atom-economic protocol for the synthesis of 1,4-skippe
Reactions of trimethylsilyl-derived iodohydrins with electron-rich π-systems
Ishai, Eti,Shamai, Sarit,Feit, Ben-Ami
, p. 434 - 438 (2007/10/03)
Reactions of trimethylsilyl-derived iodohydrins of the type R1R2CH-CH(I)OTMS, with electron-rich olefins, and the effects of certain factors on these reactions, were studied. The trimethylsilyl-derived iodohydrins were obtained in situ by reacting R1R2CH-CHO (R1 = R2 = H; R1 = H, R2 = alkyl, phenyl) with TMSI. The corresponding trimethylsilyl enol ether derivatives (R1R2C=CH-OTMS), and 1,1-diarylethylenes were the olefins used. Aldehydes of the type RCH2-CH=O reacted smoothly in the presence of TMSI to yield the condensation product RCH2-CH=C(R)-CH=O. Both RCH(-CH=CAr2)2 and the cyclic acetal 5 were obtained as main products of the RCH=O-TMSI-CH2=CAr2 reaction system, depending on the [RCHO]:[TMSI]:[CH2=CAr2] concentration ratio. The mechanisms of formation for the various main products and by-products are discussed. TMSI substitutes, formed by reacting Me3SiCl with each of several Lewis acids, were also used.
Manganese(III) or Cobalt(III)-Mediated Oxidative Radical Reactions of Terminal Dienes. One-Pot Synthesis of Bis(dihydrofuran)s
Nishino, Hiroshi,Yoshida, Tomoaki,Kurosawa, Kazu
, p. 1097 - 1107 (2007/10/02)
The reactions of terminal dienes such as 1,4-pentadienes and 1,5-hexadienes with tris(2,4-pentanedionato)manganese(III) () gave α,ω-bis(dihydrofuryl)alkanes (abbreviated bis(dihydrofuran)s, hereafter) in good yields.The reactions with tris(2,4-pentanedionato)cobalt(III) () instead of yielded the same bis(dihydrofuran)s quantitatively.The dienes also reacted with ethyl 3-oxobutanoate in the presence of manganese(III) acetate () or cobalt(III) acetate () to produce the corresponding bis(dihydrofuran)s.The reactions of 1,3-butadienes with the manganese(III) or cobalt(III) complexes afforded only mono(dihydrofuran)s and oxidative rearrangement products, but the corresponding bis(dihydrofuran)s were not formed.The reaction of 1,5-hexadienes with ethyl hydrogen malonate in the presence of did not give bis-annulated products, but mono(γ-lactone)s in moderate yields.The synthetic applications and limitations of the bis(dihydrofuran)s formation are discussed.
