Shi, Yao published the artcileComputational Chemistry-Assisted Highly Selective Radical Cascade Cyclization of 1,6-Enynes with Thiols: Access to Sulfur-Substituted 4-Enyl-2-Pyrrolidones, Quality Control of 4410-99-5, the publication is Journal of Organic Chemistry (2022), 87(15), 9479-9487, database is CAplus and MEDLINE.
In this study, an efficient method for the synthesis of sulfur-substituted 4-enyl-2-pyrrolidones I (R1 = H, 2-Me, 2-Br, 3-Cl, etc.; R2 = H, 4-Me; R3 = 4-methylphenyl, (2-chlorophenyl)methyl, furan-2-ylmethyl, etc.) was successfully developed through AIBN-promoted highly selective 5-exo-dig radical cascade cyclization of 1,6-enynes II with sulfur R3SH sources with the aid of theor. and computational chem. This protocol enables the first practical and green synthesis of an array of 4-enyl-2-pyrrolidones I in moderate-to-good yields with broad substrate scopes and high regioselectivities (>20:1). Moreover, excellent stereoselectivities have also been achieved (up to >20:1, Z/E). Most interestingly, when the sulfur source is electron-rich thiophenol, reverse stereoselectivities were discovered. In addition, the control experiments indicate that the cascade cyclization is realized by radical reactions, and the detailed reaction mechanism and regioselectivities have also been explained by theor. studies.
Journal of Organic Chemistry published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C17H14F3N3O2S, Quality Control of 4410-99-5.
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