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Reactions of N-thioacetylmorpholine anion with iodoarenes and 1-iodoadamantane by the SRN1 mechanism
✍ Scribed by Marcelo C Murguía; Roberto A Rossi
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 204 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The ~afion of N-acetylthiomorpholin¢ 2 was studied in photostimdated reactions with iodobenzene la and l-iodonaphthalene lb in DMSO, giving good yields of the substitution products 3a and 3b by the SR~I mechanism. The reaction of la with 2 is also induced with FeBr2. l-Iodoadamantane 4 did not react w~ the anion of N-acetylmotpholine, but reacted with 2 to give the substitution product 5 under irradiation. By competition experiments, acetophenune enolate ions are 1.4 times more reactive than 2 toward la and 3.3 times toward 4.
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