ISSN:
0009-2940
Keywords:
Cross coupling
;
iron-catalyzed
;
Propargylbicyclo[1.1.0]butanes
;
Allenylbicyclo[1.1.0]butanes
;
Allylbicyclo[1.1.0]butanes
;
[4.1.1]Propella-2,4-diene
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Several uncatalyzed and transition metal-catalyzed cross coupling reactions of the Grignard compounds 1c or 2c with propargylic or allylic halides were investigated. Fe(acac)3 was the most effective catalyst for the preparation of allyl-and propargylbicyclo[1.1.0]butanes 7 and 5. In the latter case, the formation of the isomeric allenylbicyclo[1.1.0]butanes 6 was also observed. Stereoelectronic factors of substituents like a trimethylsilyl group as a directing group could be utilized for the formation of either 5 or 6. A number of bicyclo[1.0.0]butanes 15-21 with two substituents in the bridgehead positions were accessible by that route as well. In the case of the bis-allenyl compound 24c, an ene-type reaction leading to the first known derivative of a [4.1.1]propella-2,4-diene 25 was observed. Base-catalyzed isomerizations of the propargylbicyclo[1.1.0]butanes 5 opened a new route to alkynylbicyclo[1.1.0]butanes 30-32.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270617
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