New Intramolecular Five-Endo-Mode Cyclization of Allenyl Aryl Ketones
- 1 February 1994
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 23 (2) , 389-392
- https://doi.org/10.1246/cl.1994.389
Abstract
A convenient preparation of allenyl aryl ketones was achieved by the Weinreb-modified Grignard reaction of N-methoxy-N-methylamides with propargylmagnesium bromide. On treatment with BF3·OEt2, the allenyl aryl ketones were converted to methylenebenzocyclopetenones via a new 5-endo-mode cyclization.Keywords
This publication has 18 references indexed in Scilit:
- A convenient synthesis of di- and trisubstituted γ-pyronesTetrahedron Letters, 1993
- A convenient synthesis of 2-exo-methylene penam, a potent intermediate for new β-lactam antibiotics synthesisTetrahedron Letters, 1991
- Synthesis of furans by silver(I)-promoted cyclization of allenyl ketones and aldehydesThe Journal of Organic Chemistry, 1991
- A novel approach to periplanone-b involving an intramolecular Diels-Alder reaction with furan-diene and allene-dienophileTetrahedron Letters, 1988
- Cycloadditionen, 9. Intramolekulare Diels‐Alder‐Reaktion bei Allencarboxaniliden; Inkorporierung des Amid‐Stickstoffatoms in Benzo‐ und Dibenzo‐kondensierten Fünf‐, Sechs‐ und SiebenringenEuropean Journal of Inorganic Chemistry, 1986
- N-methoxy-n-methylamides as effective acylating agentsTetrahedron Letters, 1981
- The preparation of a terminal allene, 3-haloallene and 3-acylallene from a propargyltrimethylsilaneThe Journal of Organic Chemistry, 1980
- Rules for ring closure: ring formation by conjugate addition of oxygen nucleophilesThe Journal of Organic Chemistry, 1977
- Phosphorus-containing products from the reaction of propargyl alcohols with phosphorus trihalides. 4. Alkyl substituent effects on oxaphospholene formationThe Journal of Organic Chemistry, 1976
- Metalation and silylation of allene: A convenient synthesis of tetrakis(trimethylsilyl)alleneJournal of Organometallic Chemistry, 1970