Reactivity of Electrophilic Allyl Halides

Abstract

y-position with various nucleophiles (alkoxides, phenoxide, thiolates and cyanide) gave rise to substituted electrophilic cyclopropanes or ring-opening products, depending upon the reaction conditions, the nature of the nucleophiles and the activating groups and the substitution pattern of the allyl halides. A kinetic study revealed that the reaction involved a nucleophilic addition as the rate determining step followed by a fast ringclosure.Reactions of allylic halides bearing two electron-withdrawing groups in i 43

Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor–Acceptor–Acceptor Cyclopropanes

“…The literature shows that when the oxy-substituent is alkoxy in nature, or even acetoxy in certain cases, the initial product can rearrange to a dihydrofuran ring 6 (Scheme 1). In fact, exceptions to this rule are rare.…”

Synthesis of Tetrahydropyrans from Propargyl Alcohols and 1,1-Cyclopropanediesters: A One-Pot Ring-Opening/Conia-ene Protocol

“…With 1,1-cyclopropanediester 1a and propargyl alcohol 5a as our exploratory substrates, we set out to find a Lewis acid capable of promoting both the nucleophilic ring-opening of the cyclopropane and subsequent Conia-ene − cyclization. While a variety of Lewis acids were screened (Table ), only In(OTf) 3 was found to perform both functions in an adequate manner.…”