72229-54-0Relevant academic research and scientific papers
Hypervalent iodine-induced nucleophilic substitution of para-substituted phenol ethers. Generation of cation radicals as reactive intermediates
Kita, Yasuyuki,Tohma, Hirofumi,Hatanaka, Kenji,Takada, Takeshi,Fujita, Shigekazu,Mitoh, Shizue,Sakurai, Hiromu,Oka, Shigenori
, p. 3684 - 3691 (2007/10/02)
A novel hypervalent iodine induced nucleophilic substitution of para-substituted phenol ethers in the presence of a variety of nucleophiles is described. UV and ESR spectroscopic studies indicate that this reaction proceeds via cation radicals, [ArH?+], as reactive intermediates generated by single-electron transfer (SET) from a charge-transfer (CT) complex of phenol ethers with phenyliodine(III) bis(trifluoroacetate) (PIFA). This is the first case that involves a radical intermediate on hypervalent iodine oxidations of aromatic compounds.
Synthesis of C-Ring-Functionalized A-Ring-Aromatic Trichothecane Analogues
Anderson, Wayne K.,Lee, George E.
, p. 501 - 506 (2007/10/02)
15,16-Dinor-4α-acetoxy-8-methoxy-6,8,10-trichothecatriene 12,13-epoxide (11) was prepared from 2α-(2-acetoxy-5-methoxyphenyl)-2β-methyl-3α-acetoxycyclopentanone (8) in three steps (bromination, DBN-induced cyclization, and spiroepoxidation).The cyclopentanone 8 was prepared from the hemiketal 6a which was prepared from 2'-acetoxy-5'-methoxyacetophenone (3f) in a reaction sequence involving the boron trifluoride catalyzed aldol addition of 1,2-bis(trimethylsilyloxy)cyclobutene followed by a trifluoroacetic acid catalyzed pinacol rearrangement of the cyclobutanone intermediate.
