N-Cyclopropylimine-1-pyrroline Rearrangement. A Novel Photochemical Reaction
- 16 November 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (25), 4087-4089
- https://doi.org/10.1021/ol016847x
Abstract
A novel aza-(vinylcyclopropane-cyclopentene) photochemical rearrangement is reported. 1-Pyrrolines are easily synthesized in good yields from N-cyclopropylimines. Hydrogen, alkyl, and aryl groups can be placed anywhere within the system, and the reaction proceeds regiospecifically.Keywords
This publication has 10 references indexed in Scilit:
- Photochemistry of Imine−Group VI Carbene Complexes: Novel Reactivity Involving a Cyclopentannulation ReactionOrganometallics, 2000
- Generation and Capture of Iminyl Radicals from Ketoxime XanthatesSynlett, 1999
- Synthetic Utility of Organometallic Reagents Derived from Group IV Metal Tetrachlorides and CH3Li. A Direct Synthesis of 2-(2-Keto-1-alkylidene)tetrahydropyrroles from 4-Alkynylamines and Acyl CyanidesOrganometallics, 1999
- A new method for the generation and capture of iminylradicalsTetrahedron Letters, 1999
- Synthesis of 2-acyl-3-chloropyrroles: Application to the synthesis of the trail pheromone of the ant Atta texanaTetrahedron, 1999
- Discovery and Synthesis of Less Common Natural HydroporphyrinsChemical Reviews, 1994
- Acid-catalyzed thermolysis of dicyclopropyl ketimines. Substituent effects on the course of the rearrangementTetrahedron Letters, 1983
- A new 2-azatricyclo[4.4.0.02,8]decenone synthesis and ketene formation by retro-Diels-Alder reactionJournal of the American Chemical Society, 1983
- AMINES FROM MIXED CARBOXYLIC-CARBONIC ANHYDRIDES: 1-PHENYLCYCLOPENTYLAMINEOrganic Syntheses, 1971
- Notes- Pyrolysis of 1,1-Dichloro-2-vinylcyclopropane Synthesis of2-ChlorocyclopentadieneThe Journal of Organic Chemistry, 1959