91798-67-3Relevant academic research and scientific papers
Reaction of Arynes with Vinyl Sulfoxides: Highly Stereospecific Synthesis of ortho-Sulfinylaryl Vinyl Ethers
Li, Yuanming,Studer, Armido
supporting information, p. 666 - 669 (2017/02/10)
The reaction of in situ generated arynes with aryl vinyl sulfoxides provides ortho-arylsulfinylaryl vinyl ethers via aryne σ-bond insertion into the S-O-bond and concomitant stereospecific S-O-vinyl migration. The cascade allows preparing di- or trisubsti
Sulfinyl-controlled Formation of Diastereoisomerically Pure Tricarbonyl(oxadiene)iron(0) Complexes and a Diastereoisomerically Pure Tetracarbonyl(alkene)iron(0) Complex
Ibbotson, Arthur,Reis, Ana C. Reduto dos,Saberi, Stephen P.,Slawin, Alexandra M. Z.,Thomas, Susan E.,et al.
, p. 1251 - 1260 (2007/10/02)
The sulfonyl and sulfinyl substituted oxadienes nCH=CHC(Me)=O; R=But, Ph; n = 2,1> form stable tricarbonyliron(0) complexes.The sulfinyl complexes formed are diastereoisomerically pure and the relative stereochemistry of the tricarbonyliron(0) unit and the sulfinyl substituent in the products has been determined by an X-ray crystal structure analysis of 0tS(O)CH=CHC(Me)=O>(CO)3> 15a.Phenylsulfonylethene and phenylsulfinylethene form stable tetracarbonyliron(0) complexes.The complex formed from phenylsulfinylethene is diastereoisomerically pure and the relative stereochemistry of the tetracarbonyliron(0) unit and the sulfinyl substituent has been determined by an X-ray crystal structure analysis of 0(CO)4> 18.This reveals evidence for a through-space interaction between the oxygen atom of the sulfinyl substituent and the carbon atom of one of the metal carbonyl ligands.The X-ray crystal structure analysis of 17, a by-product in the formation of complex 18, is also reported.
Efficient Trapping of Ketone Enolates with Acrylate and β-Sulfonylacrylate Thioesters, β-Sulfonyl-, β-sulfinyl- and β-Chloro-vinyl Ketones; Facile Preparation of a Hydrindanone, cis-Dimethyloctalone, and Unsaturated 1,5-Dicarbonyl Compounds
Dancer, Robert J.,Haynes, Richard K.,Laughlin, Wendy A.,Vonwiller, Simone C.
, p. 1375 - 1389 (2007/10/02)
Tandem conjugate addition-ring closure involving reaction of the lithium enolate arising from conjugate addition of lithiated (E)-but-2-enyldiphenylphosphine oxide to 2-methyl-cyclopent-2-enone with two moles of t-butylthioacrylate generates a hydrindanol
REACTION OF β-SULFINYL AND β-SULFENYL α,β-UNSATURATED KETONES WITH DIIMINES; PREPARATION OF 1,2-DIHYDROPYRIMIDINES
Nishio, Takehiko,Tokunaga, Tatsuhiro,Omote, Yoshimori
, p. 363 - 372 (2007/10/02)
2-Acetonyl or 2-phenacyl-1,2-dihydropyrimidines (5) were obtained by the reaction of β-sulfinyl or β-sulfenyl-α,β-unsaturated ketones (2 or 3) with diimines (1).The formation of 1,2-dihydropyrimidines (5) can be explained in terms of substitution reaction
Novel Bicycloannulation via Tandem Vinylation and Intramolecular Diels-Alder Reaction of Five-Membered Heterocycles: A New Approach to Construction of Psoralen and Azapsoralen
Hayakawa, Kenji,Yodo, Mitsuaki,Ohsuki, Satoru,Kanematsu, Ken
, p. 6735 - 6740 (2007/10/02)
trans-4-(Phenylsulfinyl)-3-buten-2-one (1) was found to undergo a new versatile addition-elimination reaction with five-membered compounds such as furans, pyrroles, imidazole, pyrazole, and 6-(dimethylamino)fulvene to give an excellent yield of the corresponding trans-4-aryl-3-buten-2-ones (3).The thermal reaction of the propargyl ethers 7a,b prepared from 3a,b gave a single intramolecular Diels-Alder adduct, 8a,b, in 59percent and 38percent yields, respectively.Treatment of 7a,b with t-BuOK in refluxing tert-butyl alcohol afforded another type of Diels-Alder adduct, 10a,b, in almost quantitative yields.This bicycloannulation strategy was applied to a new synthesis of psoralen which is of current interest due to its unique photoreactivity with DNA.The acid-catalyzed reaction of sulfoxide 12, prepared from ethyl acatoacetate in high yield, with furan gave 13 in 78percent yield.The intramolecular Diels-Alder reaction of the neopentyl acetal of 13 in the presence of Pd/C followed by acid hydrolysis afforded the tricyclic ketone 18 in 38percent yield.Baeyer-Villiger oxidation and dehydrogenation of 18 completed the synthesis of psoralen (11).Furthermore, hitherto unknown azapsoralen 20 was also synthesized by this method.
