Q3(a). Stevens rearrangements of two ylides
Give products and mechanisms for the two displayed ammonium/sulfonium salts with base. [structures of the fluorenyl ammonium salt and phenacyl sulfonium salt given in the paper]
Answer in brief
(i) 9-Benzyl-9-(dimethylamino)fluorene; (ii) PhCOCH(CH₂Ph)SMe.
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CoversStevens rearrangementammonium ylidesulfonium ylideradical pair mechanism[1,2]-shift
All parts of Question 3
- 3(a) Stevens rearrangements of two ylides10 marks
- 3(b) Knoevenagel condensation10 marks
- 3(c) Erlenmeyer–Plöchl azlactone synthesis10 marks
- 3(d) Regioselective ketone alkylation10 marks