Synthesis of functionalised indolines by radical-polar crossover reactions

Functionalised indolines have been prepared by treating tetrathiafulvalene (TTF) with 2-(N-acyl-N-allylamino)benzenediazonium tetrafluoroborates. N-Benzoyl-protected substrates afford complex reaction mixtures due to competing radical cyclisation onto the benzoyl group, Acetamides react more efficie...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 10; pp. 1549 - 1558
Main Authors Murphy, JA, Rasheed, F, Gastaldi, S, Ravishanker, T, Lewis, N
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUTION
ROUTE
TRIBUTYLTIN HYDRIDE
FORMAL SYNTHESIS
CYCLIZATION
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Summary:Functionalised indolines have been prepared by treating tetrathiafulvalene (TTF) with 2-(N-acyl-N-allylamino)benzenediazonium tetrafluoroborates. N-Benzoyl-protected substrates afford complex reaction mixtures due to competing radical cyclisation onto the benzoyl group, Acetamides react more efficiently affording good yields of product alcohols when the reactions are carried out in moist acetone.
ISSN:0300-922X
1364-5463
DOI:10.1039/a607060d