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Excess of nucleophiles: (a) Möller, F. In Methoden der Organischen Chemie (Houben-Weyl), Vol. 11/1, 4th ed.; Müller, E., Ed.; Thieme Verlag: Stuttgart, 1957, 311. (b) Mousseron, M.; Jullien, J.; Jolchine, Y. Bull. Soc. Chim. Fr. 1952, 757. (c) Deyrup, J. A.; Moyer, C. L. J. Org. Chem. 1969, 34, 175. (d) Crooks, P. A.; Szyndler, R. Chem. Ind. (London) 1973, 1111.
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51
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0242389246
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note
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2 (351 mg, 0.51 mmol) was added and the reaction mixture was heated to 80°C. After 24 h., once compound 2 was consumed (TLC), the solvent was evaporated under reduced pressure and the crude reaction mixture was purified by column chromatography on silica gel to yield the amidine 6a (340 mg, 47%) and the amine 7a (36 mg, 5%).
-
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52
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0242294752
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note
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+, 263(24)
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53
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0242326254
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55
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0242389245
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56
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0030917809
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When a less hindered epoxide is prepared on the caryophyllane skeleton, normal opening products are observed:Collado, I. G.; Hanson, J. R.; Hitchcock, P. B.; Macías-Sánchez, A. J. J. Org. Chem. 1997, 62, 1965.
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