واکنش داف

واکنش داف(به انگلیسی: Duff reaction) یا فرمیل‌دار کردن آروماتیک هگزامین(به انگلیسی: hexamine aromatic formylation) یک واکنش فرمیل‌دار کردن است که در شیمی آلی برای سنتز بنزآلدئیدها با هگزامین به عنوان منبع فرمیل کربن مورد استفاده قرار می‌گیرد. ^[۱] ^[۲] ^[۳] ^[۴] ^[۵] ^[۶] این واکنش به افتخار جیمز کوپر داف نامگذاری شده‌است که بین سال‌های ۱۹۲۰ تا ۱۹۵۰ در دانشکده فناوری ، بیرمنگام فعالیت می‌نمود.

سنتز ۳٬۵-دی-ترت-بوتیل‌سالیسیل‌آلدهید : ^[۷]

و سنتز سیرینگ‌آلدهید : ^[۸]

همچنین ببینید

منابع

↑ Duff, J. C.; Bills, E. J. (1932). "273. Reactions between hexamethylenetetramine and phenolic compounds. Part I. A new method for the preparation of 3- and 5-aldehydosalicylic acids". J. Chem. Soc.: 1987. doi:10.1039/jr9320001987.
↑ Duff, J. C.; Bills, E. J. (1934). "282. Reactions between hexamethylenetetramine and phenolic compounds. Part II. Formation of phenolic aldehydes. Distinctive behaviour of p-nitrophenol". J. Chem. Soc.: 1305. doi:10.1039/jr9340001305.
↑ Duff, J. C.; Bills, E. J. (1941). "96. A new general method for the preparation of o-hydroxyaldehydes from phenols and hexamethylenetetramine". J. Chem. Soc.: 547. doi:10.1039/jr9410000547.
↑ Duff, J. C.; Bills, E. J. (1945). "71. A new method for the preparation of p-dialkylaminobenzaldehydes". J. Chem. Soc.: 276. doi:10.1039/jr9450000276.
↑ Ferguson, L. N. (1946). "The Synthesis of Aromatic Aldehydes". Chem. Rev. 38 (2): 227–254. doi:10.1021/cr60120a002. PMID 21024865.
↑ Ogata, Y.; Sugiura, F. (1968). "Kinetics and mechanism of the Duff reaction". Tetrahedron. 24 (14): 5001. doi:10.1016/S0040-4020(01)88408-8.
↑ Larrow, Jay F.; Jacobsen, Eric N. (1998), "(R,R)-N,N'-Bis(3,5-di-tert-butylsalicylaldehyde)-1,2-cyclohexanediamino Manganese(III) Chloride, a Highly Enantioselective Epoxidation Catalyst", Org. Synth., 75: 1, doi:10.15227/orgsyn.075.0001; Coll. Vol., 10: 96 {{citation}}: Missing or empty |title= (help)
↑ Allen, C. F. H.; Leubner, Gerhard W. (1951), "Syringic aldehyde", Org. Synth., 31: 92, doi:10.15227/orgsyn.031.0092; Coll. Vol., 4: 866 {{citation}}: Missing or empty |title= (help)

[1] Duff, J. C.; Bills, E. J. (1932). "273. Reactions between hexamethylenetetramine and phenolic compounds. Part I. A new method for the preparation of 3- and 5-aldehydosalicylic acids". J. Chem. Soc.: 1987. doi:10.1039/jr9320001987.

[2] Duff, J. C.; Bills, E. J. (1934). "282. Reactions between hexamethylenetetramine and phenolic compounds. Part II. Formation of phenolic aldehydes. Distinctive behaviour of p-nitrophenol". J. Chem. Soc.: 1305. doi:10.1039/jr9340001305.

[3] Duff, J. C.; Bills, E. J. (1941). "96. A new general method for the preparation of o-hydroxyaldehydes from phenols and hexamethylenetetramine". J. Chem. Soc.: 547. doi:10.1039/jr9410000547.

[4] Duff, J. C.; Bills, E. J. (1945). "71. A new method for the preparation of p-dialkylaminobenzaldehydes". J. Chem. Soc.: 276. doi:10.1039/jr9450000276.

[5] Ferguson, L. N. (1946). "The Synthesis of Aromatic Aldehydes". Chem. Rev. 38 (2): 227–254. doi:10.1021/cr60120a002. PMID 21024865.

[6] Ogata, Y.; Sugiura, F. (1968). "Kinetics and mechanism of the Duff reaction". Tetrahedron. 24 (14): 5001. doi:10.1016/S0040-4020(01)88408-8.

[7] Larrow, Jay F.; Jacobsen, Eric N. (1998), "(R,R)-N,N'-Bis(3,5-di-tert-butylsalicylaldehyde)-1,2-cyclohexanediamino Manganese(III) Chloride, a Highly Enantioselective Epoxidation Catalyst", Org. Synth., 75: 1, doi:10.15227/orgsyn.075.0001; Coll. Vol., 10: 96 {{citation}}: Missing or empty |title= (help)

[8] Allen, C. F. H.; Leubner, Gerhard W. (1951), "Syringic aldehyde", Org. Synth., 31: 92, doi:10.15227/orgsyn.031.0092; Coll. Vol., 4: 866 {{citation}}: Missing or empty |title= (help)

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