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Synthesis 2002(16): 2421-2425
DOI: 10.1055/s-2002-35227
DOI: 10.1055/s-2002-35227
PAPER
© Georg Thieme Verlag Stuttgart · New York
Observation of O→N Type Smiles Rearrangement in Certain Alkyl Aryl Nitro Compounds [1]
Further Information
Received
15 July 2002
Publication Date:
04 November 2002 (online)
Publication History
Publication Date:
04 November 2002 (online)
Abstract
Smiles rearrangements on some alkyl aryl nitro compounds having NH2 group as the nucleophile and oxygen as the leaving group are reported.
Key words
rearrangement - nucleophilic addition - cyclization - isomerization - nitro compound
DRF Publication No. 212.
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2a
Truce WE.Kreider EM.Brand WW. Org. React. 1971, 18: 99 -
2b
Bunnett JF.Zahler RE. Chem. Rev. 1951, 49: 273 -
3a
Bayles R.Johnson MC.Maisey RF.Turner RW. Synthesis 1977, 31 -
3b
Baker WR. J. Org. Chem. 1983, 48: 5140 -
3c
Neumeyer JL.Gao Y.Kula NS.Baldessariu RJ. J. Med. Chem. 1990, 33: 3124 - 4
Davies SG.Hume WE. Tetrahedron Lett. 1195, 36: 2673 - 5
Soukri M.Lazar S.Akssira M.Guillaumet G. Org. Lett. 2000, 2: 1557 - 6 For example see:
Cao B.Park H.Joullie MM. J. Am. Chem. Soc. 2002, 124: 520 ; during the preparation of the compound 26 the authors report the formation of an unidentified aryl amine. We believe that the undesired aryl amine is presumably the structure 28 a product of Smiles rearrangement via the intermediate 27 (Figure 2) - 7
Bischofberger N.Waldmann H.Saito T.Simon ES.Lees W.Bednarski MD.Whitesides GM. J. Org. Chem. 1988, 53: 3457 - Similar studies on primary acyclic amines have been reported although under different conditions:
-
8a
Knipe AC.Sridhar N. Synthesis 1976, 606 -
8b
Mutai K.Kobayashi K. Bull. Chem. Soc. Jpn. 1981, 54: 462 - A similar amino-ethanol substrate undergoing Smiles rearrangement in a polyfunctional vinylthiohalobenzene substrate has been reported:
-
9a
Amosova SV.Gostevsgaya VI.Gavrilova GM.Afonin AV.Toryashinova DD. Zh. Org. Khim. 1993, 29: 2416 -
9b
Yilmaz I.Shine HJ. Gazz. Chim. Ital. 1989, 119:
References
DRF Publication No. 212.