Ring opening of aryl cyclopropyl ketones to l‐Acyl‐l,l,3‐tribromo‐ propanes and their cyclization to 2‐Aryl‐3,3‐dibromo‐2‐methoxy and ‐2‐cyanotetrahydrofurans
- 1 January 1983
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 20 (1) , 209-211
- https://doi.org/10.1002/jhet.5570200143
Abstract
The reaction of aryl cyclopropyl ketones 1 with excess bromine gave l‐acyl‐l,l,3‐tribromopropanes 2, which were cyclized to 2‐aryl‐3,3‐dibromo‐2‐methoxytetrahydrofurans 3 on treatment with alkaline in aqueous methanol. 2‐Aryl‐3,3‐dibromo‐2‐cyanotetrahydrofurans 5 were obtained by the reactions of 2 with sodium cyanide.Keywords
This publication has 9 references indexed in Scilit:
- Ring opening of cyclopropyl ketones by trimethylsilyl iodideThe Journal of Organic Chemistry, 1981
- Synthesis of Reduced Furans and 3(2H)-Dihydrofuranones with Manipulable FunctionalityHETEROCYCLES, 1980
- The Formation of 1,2-Diselenol-5-one and 5,6-Dihydro-4H-1,3-selenazin-4-one Derivatives from DiphenylcyclopropenoneHETEROCYCLES, 1980
- REACTION OF AMIDOXIMES WITH DIPHENYLCYCLOPROPENONE. SYNTHESIS OF 2-ARYL-5,6-DIPHENYLPYRIMIDIN-4-ONESChemistry Letters, 1979
- Electrophilic cyclopropanes in organic synthesisAccounts of Chemical Research, 1979
- Reactions of Azomethine Derivatives. IV. The Synthesis of 2,3,5-Trisubstituted 2-Pyrrolin-4-ones and Their Oxidation to 2,4,5-Trisubstituted 1,3-Oxazin-6-onesBulletin of the Chemical Society of Japan, 1978
- The synthesis of 1‐(t‐butyl)‐2‐benzoylazetidineJournal of Heterocyclic Chemistry, 1969
- Heterolytische Anlagerungen an Acetylen-Verbindungen, 2. Mitt.: Einwirkung von N-Bromsuccinimid auf 4-Phenyl-3-butin-1-ol oder 3-Phenyl-2-propin-1-ol in EssigsäureMonatshefte für Chemie / Chemical Monthly, 1967
- An Improved Synthesis of Cyclopropyl Phenyl Ketone and Related SubstancesJournal of the American Chemical Society, 1957