Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, I have read and accept the Wiley Online Library Terms and Conditions of Use, https://doi.org/10.1002/9781118939901.ch7. Find more information about Crossref citation counts. without permission from the American Chemical Society. 9/21/2013 11:30 AMPrepared by Sagar Divetiya 4 Some reactions Ester Ketone Carboxylic acid Carboxylic acid Ester Alkoxide Hydroxide α-halogenated 5. Files available from the ACS website may be downloaded for personal use only. If you have previously obtained access with your personal account, please log in. Second, upon irreversible deprotonation, the tertiary α,α-dichlorocyclobutanols underwent a ring-contraction reaction (i.e., quasi-Favorskii rearrangement) to form structurally diverse cyclopropanes in moderate to good yields. Find more information on the Altmetric Attention Score and how the score is calculated. Substrates include ketones that might be candidates for a normal Favorskii rearrangement, because even these compounds can undergo a quasi‐Favorskii reaction under the right circumstances, as illustrated in the chapter. In the presence of an alkoxide base, the rearrangement leads to the formation of an ester. The reaction proceeds through the semi-benzilic like mechanism. The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Substrates include ketones that might be candidates for a normal Favorskii rearrangement, because even these compounds can undergo a quasi‐Favorskii reaction under the right circumstances, as illustrated in the chapter. Electronic Supporting Information files are available without a subscription to ACS Web Editions. 2. These metrics are regularly updated to reflect usage leading up to the last few days. http://pubs.acs.org/page/copyright/permissions.html. Please check your email for instructions on resetting your password. Department of Chemistry, Rice University, BioScience Research Collaborative, 6500 Main Street, Rm 380, Houston, Texas 77030, United States, Synthesis of Highly Substituted Cyclopropanes via the Quasi-Favorskii Rearrangement of α,α-Dichlorocyclobutanols, Your Mendeley pairing has expired. 3. You’ve supercharged your research process with ACS and Mendeley! These synthetic strategies are illustrated with examples in the chapter. The method includes the combination two chemical transformations starting from α,α-dichlorocyclobutanones prepared via the [2 + 2] Staudinger ketene cycloaddition between either terminal- or cis-olefins and dichloroketene. There are cases in which α-haloketones with no ’-H atom undergo the Favorskii rearrangement and gives the same type of rearranged products. Stereochemistry Involved in the Favorskii Rearrangement, Beckmann Rearrangement – Examples, Detailed mechanism, What is Inductive Effect? For example. Chem. 1. Working off-campus? A. Favorskii, J. Prakt. One of the most common uses of the Favorskii rearrangement is the ring contractions for cyclic compounds. Quasi-, homo-, and oxy-Favorskii rearrangements and other ring transformations under Favorskii reaction conditions leading to intramolecular nucleophilic ring closure and other unexpected structures are covered. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. The reaction is known as Favorskii rearrangement. Notify me of follow-up comments by email. The reaction mechanism of Favorskii Rearrangement involves the following steps: 1. You have to login with your ACS ID befor you can login with your Mendeley account. The direct evidence supporting the Favorskii rearrangement mechanism has been obtained from 14C-labelling studies. These synthetic strategies are illustrated with examples in the chapter. In cyclic α-halo ketones, the rearrangement leads to ring contraction. This indicates that the rearrangement occurs through the same cyclopropanone intermediate (C) for both the isomeric -heloketones (A and B).