## Per-n Praaa.
Vinyl cations, 22 a 1,2-hydride shift in the solvolysis of 3-methyl-1-buten-2-yl triflate
✍ Scribed by Klaus-Peter Jäckel; Michael Hanack
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 137 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Recently we reprted about the first example of a 1.2-hydride shift durmg the generation of a vrnyl cation, a process well known for trlsubstituted car&mum ions 2) :Thls was obsermildurlng the solvolys~s of cls-and trans-3-cyclop~l-2-propen-2-yl-trifl~~~esulfo~~(tnflate)3! --The 1.2-hydride shLft was found to be a c r o s s the double bond.
📜 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
Despite the extensive amount of research on nonenzymatic [1,2]-hydride shifts.2 there have been particularly few reports on similar transfers related to carbohydrates.3 We wish to report here the novel example of the stereoselective [1,2]-hydride shifts which occured in the reactions of methyl 3-0-m
## Swrnnary: ~icarbonyZ-I3-methoxycyctohe~-2,4-dien-l-yl)-iro~l~l+~ PFcfl-) 2 reacts with a variety of nucleophiles to give 5-substi-&ted cyclohex-2-enones. 2 is sham to be a useful precursor for a convergent synthesis of 5-substituted cyclohcx-2-enones and to be synthetically equivalent to the 5