919792-58-8Relevant academic research and scientific papers
Semipinacol Rearrangement Induced by Cleavage of Dibromocyclopropane
Kurimoto, Michitaka,Nakajima, Daisuke,Nishiyama, Yoshitake,Yokoshima, Satoshi
supporting information, p. 4108 - 4111 (2020/05/08)
A novel semipinacol rearrangement using dibromocyclopropanes as sources of carbocations was developed. Heating dibromocyclopropanes bearing a 1-hydroxyalkyl group with silver perchlorate and 2,6-lutidine induced cleavage of the cyclopropane ring to form allyl cations, which underwent 1,2-shift of a substituent at the α-position of the hydroxy group to give β,γ-unsaturated carbonyl compounds having a quaternary carbon at the α-position. Because the products have convertible functional groups such as bromo, vinyl, and formyl groups, the method is expected to be applicable to the synthesis of various molecules.
Electrophilic Trifluoromethylthiolation/Semipinacol Rearrangement: Preparation of β-SCF3 Carbonyl Compounds with α-Quaternary Carbon Center
Xi, Chao-Chao,Chen, Zhi-Min,Zhang, Shu-Yu,Tu, Yong-Qiang
, p. 4227 - 4230 (2018/07/29)
A new and modular electrophilic trifluoromethylthiolation/semipinacol rearrangement of allylic silyl ethers has been developed under mild conditions. This approach allows the formation of a number of β-SCF3 carbonyl compounds with a cyclic and all-carbon quaternary center framework in moderate to good yields. It should be noted that this achievement is a metal-free process and just requires the use of simple acetyl chloride as an acidic promoter. Additionally, an interesting H-migration in competition with aryl-migration process was revealed.
Highly selective coupling of alkenes and aldehydes catalyzed by [Ni(NHC){P(OPh)3}]: Synergy between a strong σ donor and a strong π acceptor
Ho, Chun-Yu,Jamison, Timothy F.
, p. 782 - 785 (2007/10/03)
(Chemical Equation Presented) Give and take: Both a strong electron donor (1) and a strong electron acceptor (P(OPh)3) are necessary for a highly selective, nickel-catalyzed coupling reaction between alkenes, aldehydes, and silyl triflates (see
Phosphazene base-promoted functionalization of aryltrimethylsilanes
Suzawa, Koichi,Ueno, Masahiro,Wheatley, Andrew E. H.,Kondo, Yoshinori
, p. 4850 - 4852 (2007/10/03)
The activation of Ar-Si bonds in aryltrimethylsilane was investigated using a catalytic amount of t-Bu-P4 base and selective functionalizations of aryltrimethylsilanes in the absence of strong electron withdrawing groups on the aromatic rings were accomplished. The Royal Society of Chemistry 2006.
