An unexpected one-pot synthesis of 7-isopropyl-3,3-dimethyl-10 H-spiro(indoline-2,9 -phenanthren)-10 -one

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The reaction of two commercially available compounds, phenanthrenequinone and 2,6-dialkylaniline (alkyl = Me, iPr), catalyzed by formic acid, in refluxing methanol, gave rise exclusively to 10-(2,6-dialkyl-phenylimino)-10H-phenanthren-9-one compounds (alkyl = Me (1), iPr (2)). In refluxing toluene, and when diisopropylaniline is employed, the heterocyclic compound 7-isopropyl-3,3-dimethyl-10'H-spiro(indoline-2,9'-phenanthren)-10'-one ( 3) was unexpectedly prepared as the major reaction product, in the presence of catalytic amounts of various Bronsted acids. DFT calculations indicate that the conversion of 2 into 3 involves a sigmatropic rearrangement as rate limiting step with a high energy barrier (25-28 kcal/mol), in agreement with the requirement of high reaction temperatures.
Publisher
ARKAT USA INC
Issue Date
2009
Language
English
Article Type
Article
Keywords

MOLECULAR-ORBITAL METHODS; GAUSSIAN-TYPE BASIS; REDUCTIVE AMINATION; ETHYLENE POLYMERIZATION; ALPHA-OLEFINS; (ALPHA-DIIMINE)NICKEL(II) CATALYSTS; LIVING POLYMERIZATION; ORGANIC-MOLECULES; METAL CATALYSTS; ALDEHYDES

Citation

ARKIVOC, pp.95 - 111

ISSN
1551-7004
URI
http://hdl.handle.net/10203/98292
Appears in Collection
CH-Journal Papers(저널논문)
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