几种羰基化合物的有机光化学反应研究及应用
|
摘要
分别从分子间吸氢反应、Norrish I型光化学反应、NorrishⅡ型光化学反应、羰基化合物与烯烃的加成反应以及(γ±n)-氢的羰基化合物的光化学重排反应对羰基化合物的有机光化学反应进行简单阐述,并介绍呋喃类、α-二羰基化合物、醛甾酮类等羰基化合物光化学反应的合成工艺及应用。
Respectively from intermolecular hydrogen absorption reaction,Norrish type I photochemical reaction,Norrish Ⅱ photochemical reaction,carbonyl compounds and the addition reaction of olefins and(γ ± n)-hydrogen rearrangement of photochemical reaction of carbonyl compounds in organic photochemical reaction of carbonyl compounds were briefly introduced,and furan,alpha dicarbonyl compounds,aldosterone carbonyl compounds,such as the synthesis process and application of photochemical reaction were presented.
Respectively from intermolecular hydrogen absorption reaction,Norrish type I photochemical reaction,Norrish Ⅱ photochemical reaction,carbonyl compounds and the addition reaction of olefins and(γ ± n)-hydrogen rearrangement of photochemical reaction of carbonyl compounds in organic photochemical reaction of carbonyl compounds were briefly introduced,and furan,alpha dicarbonyl compounds,aldosterone carbonyl compounds,such as the synthesis process and application of photochemical reaction were presented.
引文
[1]De Feyter S,Diau E W G,Zewail A H.Angew.Chem.Int.Ed.,2000,39:260-263.
[2]Wagner P J.Acc Chem.Res,1971(4):168-177.
[3]Gilbert A,Baggott J.Essentials of Molecular Photochemistry.Boca Raton,FL.CRC Press,1991.
[4]Horspool W,Armesto D.Organic Photochemistry.A Comprehensive Treatment.EllisHorwood Limited,1992.
[5]Wagner P J.in CRC Handbook of Organic Photochemistry and Photobiology(eds.Horspool WM,Song P S).Boca Raton:CRC Press,1995.
[6]Turro N J.Modern Molecular Photochemistry[M].University Science Books,1990.
[7]Walling C,Clark R T.J Am Chem Soc,1974,96:4530.
[8]Baum A A.J Am Chem Soc,1972,94:6866.
[9]Fischer H.Pure Appl Chem,1975,41:475.
[10]Walling C.Pure Appl Chem,1976,15:69.
[11]DeCosta,D.P.A.K.Bennett,et al.The Norrish Type II Photofragmentation of Esters Induced by Intramolecular Electron Transfer[J].J Am Chem Soc,1999,121(15):3785-3786.
[12]Norrish,R.J.,Crone,W.H.G.,Saltmarsh,O.D.J.Am.Chem.Soc,1934,J6(7):1644.
[13]Norrish,R.J.W.J.Am.Chem.Soc.,1938,60(6):1513.
[14]Roy,S.C.,S.Adhikari.Stereoselective total synthesis of(±)Paulownin and(±)-Isogmelinol through radical annulation route[J].Tetrahedron,1993,49(37):8415-8422.
[15]Newcomb,et al.Adjusting the Top End of the Alkyl Radical Kinetic Scale.Laser Flash Photolysis Calibrations of Fast Radical Clocks and Rate Constants for Reactions of Benzeneselenol[J].Org Chem,1999,64(4):1225-1231.
[16]Cottier,L.,G.Descotes.Syntheses stereoselectives des isomeres cinetiques et thermodynam-iques d'alcoxy-spirocetals et de trioxabis-spirocetals[J].Tetrahedron,1985,41(2):409-412.
[17]Cottier,L.G.Descotes,et al.Synthese photochimique et etude structurale d'alcoxy-spirocetals et de trioxa-bis-spirocetals[J].Tetrahedron,1981,37(14):2515-2524.
[18]Zhou,B.,P.J.Wagner.Long-range triplet hydrogen abstraction.Photochemical formation of 2-tetralols from.beta.-arylpropiophenones[J].J.Am Chem Soc,1989,111(17):6796-6799.
[19]Hornback,J.M.M.L.Poundstone,etal.Photochemical cyclization of omethylphenyl 1,3-diketones[J].Org Chem,1988,53(24):55975601.
[20]Griesbeck,A.G.,A.Henz,et al.Photochemistry of N-phthaloyl derivatives of electron-donor-substituted amino acids[J].Tetrahedron.,1994,50(3):701-714.
[21]Balcar,J.G.Chrisam,et al.Reaktivitt von stickstoff-heterocyclen genenüber cyclooctin als dienophil[J].Tetrahedron Letters,1983,24(14):1481-1484.
[22]Sowa,C.E,J.Kopf,et al.Syntheses of sugar-derived heterotricyclic lactams[J].Chem Soc,Chemical Communications,1995(2):211212.
[23]Coyle,J.D.,L.R.B.Bryant.Synthesis of diazaheterocycles with a bridgehead nitrogen by photocyclisation of N-substituted alicyclic imides[J].Chemical Society,Perkin Transactions,1983(1):28572865.
[24]张成路,周龙,李元东,等.(1R,5S)-3-羟基二环(3.1.0)己基6-基(苯基)甲酮的合成及其NorrishⅡ型光化学反应研究[J].有机化学,2011,31(12):2145-2150.
[25]Ayral-Kaloustian,S.,Agosta,W.C.Absence of Stereoelectronic Control in the Photochemistry of two Diastereomericβ,γ-Epoxy Ketones[J].J.Am.Chem.Soc.,1980,102(1):314-323.
[26]Murray,R.K.,Morgan,T.K.,Polley,J.A.S.The Photochemistry ofβ,γ-Epoxy Cyclic Ketones[J].J.Am.Chem.Soc.,1975,97(4):938-940.
[27]汪春晖.NorrishⅡ型光化学反应合成苯并呋喃类新木脂素的研究[D].哈尔滨:哈尔滨工业大学物理化学,2011.
[28]Barton,D.H.R.,J.M.Beaton,et al.A New Photochemical Reaction.[J]J Am Chem Society,1960,82(10):2640-2641.
[29](a)F.D.Popp,Adv.Hetewcycl.Chem.,1975,18,1;(b)M.A.Shvekhgeimer,Khim.Geterotsikl.Soedin.,1996:291.
[30]M.N.Elinson,A.I.Ilovaisky,A.S.Dorofeev,V.M.Merkulova,N.0.Stepanov,F.M.Miloserdov,Y.N.Ogibin and G.I.Nikishin[J].Tetrahedron,2007,63:10543.
[2]Wagner P J.Acc Chem.Res,1971(4):168-177.
[3]Gilbert A,Baggott J.Essentials of Molecular Photochemistry.Boca Raton,FL.CRC Press,1991.
[4]Horspool W,Armesto D.Organic Photochemistry.A Comprehensive Treatment.EllisHorwood Limited,1992.
[5]Wagner P J.in CRC Handbook of Organic Photochemistry and Photobiology(eds.Horspool WM,Song P S).Boca Raton:CRC Press,1995.
[6]Turro N J.Modern Molecular Photochemistry[M].University Science Books,1990.
[7]Walling C,Clark R T.J Am Chem Soc,1974,96:4530.
[8]Baum A A.J Am Chem Soc,1972,94:6866.
[9]Fischer H.Pure Appl Chem,1975,41:475.
[10]Walling C.Pure Appl Chem,1976,15:69.
[11]DeCosta,D.P.A.K.Bennett,et al.The Norrish Type II Photofragmentation of Esters Induced by Intramolecular Electron Transfer[J].J Am Chem Soc,1999,121(15):3785-3786.
[12]Norrish,R.J.,Crone,W.H.G.,Saltmarsh,O.D.J.Am.Chem.Soc,1934,J6(7):1644.
[13]Norrish,R.J.W.J.Am.Chem.Soc.,1938,60(6):1513.
[14]Roy,S.C.,S.Adhikari.Stereoselective total synthesis of(±)Paulownin and(±)-Isogmelinol through radical annulation route[J].Tetrahedron,1993,49(37):8415-8422.
[15]Newcomb,et al.Adjusting the Top End of the Alkyl Radical Kinetic Scale.Laser Flash Photolysis Calibrations of Fast Radical Clocks and Rate Constants for Reactions of Benzeneselenol[J].Org Chem,1999,64(4):1225-1231.
[16]Cottier,L.,G.Descotes.Syntheses stereoselectives des isomeres cinetiques et thermodynam-iques d'alcoxy-spirocetals et de trioxabis-spirocetals[J].Tetrahedron,1985,41(2):409-412.
[17]Cottier,L.G.Descotes,et al.Synthese photochimique et etude structurale d'alcoxy-spirocetals et de trioxa-bis-spirocetals[J].Tetrahedron,1981,37(14):2515-2524.
[18]Zhou,B.,P.J.Wagner.Long-range triplet hydrogen abstraction.Photochemical formation of 2-tetralols from.beta.-arylpropiophenones[J].J.Am Chem Soc,1989,111(17):6796-6799.
[19]Hornback,J.M.M.L.Poundstone,etal.Photochemical cyclization of omethylphenyl 1,3-diketones[J].Org Chem,1988,53(24):55975601.
[20]Griesbeck,A.G.,A.Henz,et al.Photochemistry of N-phthaloyl derivatives of electron-donor-substituted amino acids[J].Tetrahedron.,1994,50(3):701-714.
[21]Balcar,J.G.Chrisam,et al.Reaktivitt von stickstoff-heterocyclen genenüber cyclooctin als dienophil[J].Tetrahedron Letters,1983,24(14):1481-1484.
[22]Sowa,C.E,J.Kopf,et al.Syntheses of sugar-derived heterotricyclic lactams[J].Chem Soc,Chemical Communications,1995(2):211212.
[23]Coyle,J.D.,L.R.B.Bryant.Synthesis of diazaheterocycles with a bridgehead nitrogen by photocyclisation of N-substituted alicyclic imides[J].Chemical Society,Perkin Transactions,1983(1):28572865.
[24]张成路,周龙,李元东,等.(1R,5S)-3-羟基二环(3.1.0)己基6-基(苯基)甲酮的合成及其NorrishⅡ型光化学反应研究[J].有机化学,2011,31(12):2145-2150.
[25]Ayral-Kaloustian,S.,Agosta,W.C.Absence of Stereoelectronic Control in the Photochemistry of two Diastereomericβ,γ-Epoxy Ketones[J].J.Am.Chem.Soc.,1980,102(1):314-323.
[26]Murray,R.K.,Morgan,T.K.,Polley,J.A.S.The Photochemistry ofβ,γ-Epoxy Cyclic Ketones[J].J.Am.Chem.Soc.,1975,97(4):938-940.
[27]汪春晖.NorrishⅡ型光化学反应合成苯并呋喃类新木脂素的研究[D].哈尔滨:哈尔滨工业大学物理化学,2011.
[28]Barton,D.H.R.,J.M.Beaton,et al.A New Photochemical Reaction.[J]J Am Chem Society,1960,82(10):2640-2641.
[29](a)F.D.Popp,Adv.Hetewcycl.Chem.,1975,18,1;(b)M.A.Shvekhgeimer,Khim.Geterotsikl.Soedin.,1996:291.
[30]M.N.Elinson,A.I.Ilovaisky,A.S.Dorofeev,V.M.Merkulova,N.0.Stepanov,F.M.Miloserdov,Y.N.Ogibin and G.I.Nikishin[J].Tetrahedron,2007,63:10543.