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2005
Indole derivatives
R 0140
Effect of Sodium Naphthalenide, a Key SET Reagent, on 3-Substituted Indoles.
Six indole derivatives possessing electron-donating or electron-withdrawing substit11- 131 —
uents are subjected to reaction with the single electron transfer (SET) reagent sodium
naphthalenide. Except indoles bearing an electron-donating substituent all other compounds are reactive. The reactions between sodium naphthalenide and (VIII), (IX), and
(XI) are highly selective but the selectivity is almost lost in the reaction between (I) and
(II). An explanation for this feature may be the result of the formation of an
3-alkylidene-3H-indolium cation as well as the formation of an intermediate radical
anion which can react in several ways to form products (III)—(VI). — (BANERJI*,
A.; BANDYOPADHYAY, D.; BASAK, B.; Heterocycles 63 (2004) 10, 2371-2377;
Dep. Chem., Univ. Calcutta, Calcutta 700 009, India; Eng.) — H. Hoennerscheid
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