## Abstract The tricyclic lactams 4aβh, possessing a bicyclo[2.2.2]octadiene moiety, obtained by intramolecular DielsβAlder reaction of the vinylidene malondiamides 1aβh, generally isomerize in boiling xylene to give the new lactams 7aβh, now bearing a bicyclo[3.2.1]octadiene part. The difference i
Mechanism of the rearrangement of bicyclo[3.2.1]octadien-2-yl cations to bicyclo[3.3.0]octadien-2-yl cations
β Scribed by Masayuki Kuzuya; Harold Hart
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- French
- Weight
- 165 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Below -60' in FSOaH/SOzClF the nonamethyl bicyclo[3.2.1 loctadien-Pyl cation J, undergoes two degenerate rearrangements, circumambulation' and a 1,2-shift of the methano bridge.2 The first of these processes is much faster than the second, and is nmr-observable,' whereas the second process was detected only by labeling studies.2 When solutions of i in FSOaH/SO,ClF
π SIMILAR VOLUMES
In FSOsH/SO&lF at -50 to -100' the nonamethylbicyclo[3.2.1] octadien-2-yl cation 1 undergoes an nmr-observable reversible exchange process which equilibrates methyls 2,3,4,6 and 7 and methyls 8 and 9, but leaves the bridgehead methyls (1 and 5) unique.l CIRCUMAMBULATION 3 This observation was ration