ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Upon treatment with organolithium compounds, 2-alkyl-4,5-dihydrofurans undergo ring opening through β-elimination leading to the corresponding 3,4-dien-1-ol. If 3-chloro-2-methyl-4,5-dihydrofuran serves as a substrate, however, no 3-chloro-3,4-dien-1-ol can be isolated though it acts as a reaction intermediate. Its formation is slow compared to subsequent replacement of halogen by the organic moiety of the alkyllithium reagent. Thus penta-3,4-dien-1-ols are formed, which may isomerize, however, under certain reaction conditions affording terminal acetylenes. These as well as their allene precursors can be converted with sodium in ammonia into pent-4-en-1-ol or, respectively, pent-3-en-1-ol derivates.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19750580227
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