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For preparations of alkyl cycloprop-2-ene carboxylates: a
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For preparations of alkyl cycloprop-2-ene carboxylates: (a) Baldwin, J. E.; Villarica, K. A. J. Org. Chem. 1995, 60, 186.
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For a prior synthesis of cycloprop-2-ene carboxylic acid, see: a
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For a prior synthesis of cycloprop-2-ene carboxylic acid, see: (a) Nefedov, O. M.; Dolgij, I. E.; Okonnischnikova, G. P.; Schwedova, I. B. Angew. Chem., Int. Ed. Engl. 1972, 11, 929.
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22
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For syntheses of 2-silyl derivatives of cycloprop-2-ene carboxylic acid, see also: (b) Maier, G.; Hoppe, M.; Reisenauer, H. P.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1982, 21, 437.
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For syntheses of 2-silyl derivatives of cycloprop-2-ene carboxylic acid, see also: (b) Maier, G.; Hoppe, M.; Reisenauer, H. P.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1982, 21, 437.
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26
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44949247698
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Compound 3 was also prepared in similar yield with the modification that pivaloyl chloride was used in place of 1-adamantoyl chloride.
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Compound 3 was also prepared in similar yield with the modification that pivaloyl chloride was used in place of 1-adamantoyl chloride.
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27
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84987014061
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For reviews on Diels-Alder reactions of cyclopropenes, see ref 2b-d. For Diels-Alder reactions of cycloprop-2-ene carboxylates, see ref 3b and: (a) Paulini, K, Reissig, H. U. J. Prakt. Chem. Chem. Z. 1995, 337, 55
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For reviews on Diels-Alder reactions of cyclopropenes, see ref 2b-d. For Diels-Alder reactions of cycloprop-2-ene carboxylates, see ref 3b and: (a) Paulini, K.; Reissig, H. U. J. Prakt. Chem. Chem. Z. 1995, 337, 55.
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0346502724
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For other, recent examples of Diels-Alder reactions of cyclopropenes, see: f
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For other, recent examples of Diels-Alder reactions of cyclopropenes, see: (f) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406.
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(g) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron Lett. 2000, 41, 4205.
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For recent theoretical studies on the endo selectivity of cyclopropene Diels-Alder reactions, see: a
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For recent theoretical studies on the endo selectivity of cyclopropene Diels-Alder reactions, see: (a) Xidos, J. D.; Gosse, T. L.; Burke, E. D.; Poirer, R. A.; Burnell, D. J. J. Am. Chem. Soc. 2001, 123, 5482.
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Ortiz, A.; Quintero, L.; Hernández, H.; Maldonado, S.; Mendoza, G.; Bernéz, S. Tetrahedron Lett. 2003, 44, 1129.
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38
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44949089930
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For the preparations of 2-4, similar yields were obtained when 5 was added as neat material or as a ∼30% wt solution in MTBE.
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For the preparations of 2-4, similar yields were obtained when 5 was added as neat material or as a ∼30% wt solution in MTBE.
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