122663-76-7Relevant academic research and scientific papers
Convenient method for the preparation of 1-phenylthio-3-alken-1-ynes and 4-hydroxy-1-phenylthio-1,2-alkadienes from a common precursor
Ogawa, Atsushi,Sakagami, Kazunari,Shima, Akiko,Suzuki, Hitoshi,Komiya, Satsuki,Katano, Yoshinori,Mitsunobu, Oyo
, p. 6387 - 6389 (2007/10/03)
4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted the (Z)-isomers into (E)-isomers. On the other hand, the reaction of 5 with KHMDS gave the corresponding 4-hydroxy-1-phenythio-1,2-alkadienes.
Stereoselective synthesis of (Z)-α-phenoxymethylene-γ-butyrolactone and its sulfur analogues from 2-propynyloxy- or 2-propynylthiobenzene
Luo, Fen-Tair,Ko, Seng-Li,Liu, Lijun,Chen, Hui
, p. 2055 - 2066 (2007/10/03)
The preparations of (Z)-α-phenoxymethylene-γ-butyrolactone, α-phenoxymethyl-γ-butyrolactone, (Z)-α-phenylthiomethylene-γ-butyrolactone, and α-phenylthiomethyl-γ-butyrolactone derivatives from 2-propynyloxy-benzene and 2-propynylthiobenzene were described.
A Highly Regioselective Reaction of Allylic Acetates with Silylated Carbon Nucleophiles Directed by a Sulfenyl Group. Scope, Limitation, and Mechanistic Aspects
Kudo, Kazuaki,Hashimoto, Yukihiko,Houchigai, Hitoshi,Hasegawa, Masaki,Saigo, Kazuhiko
, p. 848 - 856 (2007/10/02)
α-(Sulfenylmethyl)allyl acetates reacted with silylated carbon nucleophiles in the presence of a catalytic amount of TMSOTf to give products substituted at the α-position of the sulfenylmethyl group in moderate to good yields with high regioselectivity.The theoretical calculation on an intermediate cationic species indicated that an episulfonium ion was a stable form; the observed regioselectivity was rationalized qualitatively on the basis of the coefficients of LUMO of the cation.Some transformations of the products were also demonstrated.
Stereoselectivity in the sigmatropic rearrangement of eight- and nine-membered cyclic allylsulfonium ylides. Synthesis of vinyl- substituted butyro- and valerolactones
Kido, Fusao,Sinha, Subhash C.,Abiko, Toshiya,Watanabe, Masataka,Yoshikoshi, Akira
, p. 4887 - 4906 (2007/10/02)
The rhodium (II) acetate-catalyzed [2,3]sigma-tropic rearrangement of the diazo malonates of (z)-4-phen-ylthio-2-buten-1-ol derivatives 6 afforded vinyl-substituted butyrolactones 10 in a highly stereoselective manner, while the rearrangement of the diazo malonates of homologues, (z)-5-phenylthio-3-penten-1-ol derivatives 9, yielded vinyl-substituted valerolactones 13 and 14 in the predominance of the formers. A stereochemically fixed substituent R in 9 was found to be an important factor resulting to high stereoselectivity in the latter rearrangement as shown by using diazo malonate 20b as substrate.
STEREOSELECTIVE SYNTHESIS OF CONTIGUOUSLY SUBSTITUTED BUTYROLACTONES BASED ON THE CYCLIC ALLYLSULFONIUM YLIDE REARRANGEMENT
Kido, Fusao,Sinha, Subhash C.,Abiko, Toshiya,Yoshikoshi, Akira
, p. 1575 - 1578 (2007/10/02)
α-Diazomalonates of (Z)-4-phenylthio-2-buten-1-ol homologues (2) stereoselectively provided γ-alkyl-α-ethoxycarbonyl-α-phenylthio-β-vinylbutyrolactones (1) by the sigmatropic rearrangement of cyclic sulfonium ylides (3) intramolecularly generated the
