ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Attempted Synthesis of Nonafulvenes and of NonaheptafulvaleneThe reaction of cyclononatetraenide with α-bromobenzyl acetate (6) as well as with 1,1-dihalodimethylether gives at -50°, instead of the expected cyclononatetraenes, bicyclo[6.1.0]nona-2,4,6-triene derivatives 10d and 16 (Scheme 3 and 5, respectively). It seems that in some cases the well known thermally disrotative valence isomerization of cyclononatetraenes 7 to 3a, 7a-dihydroindenes 8 is much slower than the formation of bicyclo[6.1.0]nona-2,4,6-trienes of the type 10 and 16. This type of reaction hurts the Woodward-Hoffmann rules.Possible precursors of the attractive nonaheptafulvalene are prepared by reaction of acetoxy-tropylium fluoborate (19a) as well as of bromo-tropylium bromide (19b) with lithium-cyclononatetraenide (Scheme 8). So far, the attempted gas-phase pyrolysis of the precursors 21a and 21b failed to give nonaheptafulvalene (5).
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19790620311
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