Theoretical Study of the Mechanism of the Formation of 3-Unsubstituted 4,4-Disubstituted β-Lactams by Silver-Induced Ring Expansion of Alkoxycyclopropylamines:  A New Synthetic Route to 4-Alkoxycarbonyl-4-alkyl-2-azetidinones

2003 ◽  
Vol 68 (17) ◽  
pp. 6685-6689 ◽  
Author(s):  
Pablo Campomanes ◽  
M. Isabel Menéndez ◽  
Tomás L. Sordo
Keyword(s):  
Theoretical Study ◽  
Ring Expansion ◽  
Synthetic Route

Oxidative Dearomatization and Sigmatropic 1,3-Acyl Shift in Excited State: Aromatics to Embellished cis-Hydrindanes

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1633-1642
Author(s):  
Vishwakarma Singh ◽  
Raghaba Sahu
Keyword(s):  
Excited State ◽  
Ring Expansion ◽  
Synthetic Route ◽  
Oxidative Dearomatization ◽  
Key Features

A stereoselective synthetic route to embellished cis-hydrindanes from simple aromatic precursors is described. Oxidative dearomatization, ring expansion, and photochemical 1,3-acyl shift are the key features of our approach. Oxidative dearomatization of o-(hydroxymethyl)phenols followed by π4s + π2s cycloaddition furnishes bicyclo[2.2.2]octanes with contiguous keto epoxide groups, which upon ring expansion lead to bicyclo[3.2.2]nonanes endowed with a β,γ-enone chromophore. Unbridging of bicyclo[3.2.2]nonanes upon singlet excitation furnishes embellished cis-hydrindanes.

The Dowd–Beckwith ring expansion: a theoretical study

2004 ◽  
Vol 45 (47) ◽  
pp. 8691-8694 ◽  
Author(s):  
Diego Ardura ◽  
Tomás L. Sordo
Keyword(s):  
Theoretical Study ◽  
Ring Expansion

scholarly journals New Syntheses and Ring Expansion Reactions of Cyclobutenimines

2010 ◽  
Vol 63 (12) ◽  
pp. 1656 ◽  
Author(s):  
Ernst Schaumann ◽  
Gerrit Oppermann ◽  
Michael Stranberg ◽  
Harold W. Moore
Keyword(s):  
Carbonyl Group ◽  
Ring Expansion ◽  
Synthetic Route ◽  
Tertiary Alcohols ◽  
Ring Enlargement ◽  
Alkyl Derivatives

Two routes are reported for the synthesis of iminocyclobutenones having N-(het)aryl substitution: an addition/substitution sequence starting with cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein’s reagent and subsequent deprotonation under non-hydrolytic conditions. Lithium organyls were found to add to the remaining carbonyl group. The resulting tertiary alcohols undergo ring enlargement on heating in xylene to give 4-aminophenols, 4-amino-1-naphthols, or cyclopenta-annulated quinolines from 4-vinyl, 4-aryl, and 4-alkynyl derivatives, respectively.

A theoretical study on the ring expansion of NHCs by silanes

2013 ◽  
Vol 42 (31) ◽  
pp. 11035 ◽  
Author(s):  
Kalon J. Iversen ◽  
David J. D. Wilson ◽  
Jason L. Dutton
Keyword(s):  
Theoretical Study ◽  
Ring Expansion

Theoretical study on the reaction mechanism of cyclopropenylidene with azacyclopropane: ring expansion process

2014 ◽  
Vol 145 (7) ◽  
pp. 1109-1115 ◽  
Author(s):  
Xiaojun Tan ◽  
Weihua Wang ◽  
Ying Jing ◽  
Fang Wang ◽  
Ping Li
Keyword(s):  
Reaction Mechanism ◽  
Theoretical Study ◽  
Ring Expansion ◽  
Expansion Process

Ring Expansion of 2‐(α‐Hydroxyalkyl)azetidines: A Synthetic Route to Functionalized Pyrrolidines

2008 ◽  
Vol 2008 (19) ◽  
pp. 3286-3297 ◽  
Author(s):  
François Durrat ◽  
Monica Vargas Sanchez ◽  
François Couty ◽  
Gwilherm Evano ◽  
Jérôme Marrot
Keyword(s):  
Ring Expansion ◽  
Synthetic Route
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