Two Way Reactivity of 1,1-Dichloro-2-(chloromethyl)cyclopropane in Basic Medium: A Simple Synthesis of 1,1-Bis(aryloxy)-2-methylenecyclopropanes
作者:Andrzej Jończyk、Irena Kmiotek-Skarżyńska
DOI:10.1055/s-1992-26285
日期:——
1,1-Dichloro-2-(chloromethyl)cyclopropane (1) reacts with phenols 2a-l, alcohols 2m,n or thiophenol (2o) in different base/solvent systems, to form either 2-(aryloxymethyl)-1,1-dichlorocyclopropanes 3 and/or 1,1-bis(aryloxy)-2-methylenecyclopropanes 4. Reaction of 1 with piperidine (2p) and sodium cyanide (2q) affords 1,1-dichloro-2-(piperidinomethyl)cyclopropane (3p) and 1, 1-dichloro-2-(cyanomethyl)cyclopropane (3q), respectively. The kind of the products formed depends on the reaction conditions and the structure of the heteronucleophile.
1,1-二氯-2-(氯甲基)环丙烷 (1) 与酚类 2a-l、醇类 2m,n 或硫酚 (2o) 在不同的碱/溶剂体系中反应,生成 2-(芳氧甲基)-1,1-二氯环丙烷 3 和/或 1,1-双(芳氧)-2-亚甲基环丙烷 4。1 与哌啶 (2p) 和氰化钠 (2q) 反应,分别得到 1,1-二氯-2-(哌啶甲基)环丙烷 (3p) 和 1,1-二氯-2-(氰甲基)环丙烷 (3q)。生成的产物类型取决于反应条件和异核亲核试剂的结构。