ISSN:
0009-2940
Keywords:
Metallated methyl isopropenyl ether
;
Tetrahydrofurans
;
1-Oxabicyclo[4.3.0]heptanes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Methyl isopropenyl ether (1) has been metallated at low temperature with a 1:1 molar mixture of n-BuLi/t-BuOK in THF-hexane, and subsequently functionalized with a variety of electrophilic reagents. At temperatures higher than - 30°C, the metallated methyl isopropenyl ether (2) decomposes with formation of allene. When the suspension of 2 is allowed to warm up to room temperature in the presence of an additional equivalent of n-BuLi, the intermediary allene is converted into 1-propynyllithium (2c), which reacts with propylthiocyanate to give 1-propylthio-1-propyne (4). Some of the functionalization products were subjected to acidic hydrolysis affording the expected methyl ketones.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19971300107
