Photochemical intramolecular h-abstractions: A brief account on their synthetic utility

Current Organic Chemistry

Volumn 19, Issue 22, 2015, Pages 2156-2195

  Dalal, Aarti ^a   Khanna, Radhika ^a   Kumar, Dinesh ^a   Jindal, Pooja ^a   Chaudhary, Ashu ^a   Kamboj, Ramesh C ^a  

^a KURUKSHETRA UNIVERSITY   (India)

Author keywords

Cyclization; Functionalization; H abstraction; Irradiation; Photochemical approach

Indexed keywords

ABSTRACTION REACTIONS; CYCLIZATIONS; FUNCTIONALIZATIONS; H-ABSTRACTION; PHOTOCHEMICAL APPROACH; PHOTOCHEMICAL BEHAVIORS; PHOTOCHEMICALS; SYNTHETIC ORGANIC CHEMISTRY; SYNTHETIC UTILITY; [CARBONYL;

CHROMOPHORES;

EID: 84947749313     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272819666150730215450     Document Type: Article

References (244)

1. Norrish, R. G. W.; Appleyard, M. E. S. Primary photochemical reactions. Part IV. Decomposition of methyl ethyl ketone and methyl butyl ketone. J. Chem. Soc., 1934, (0), 874-880.
2. Bamford, C. H.; Norrish, R. G. W. Primary photochemical reactions. Part VII. Photochemical decomposition of isovaleraldehyde and di-n-propyl ketone. J. Chem. Soc., 1935, (0), 1504-1511.
3. McMillan, G. R.; Calvert, J. G.; Pitts, J. N. Detection and lifetime of enolacetone in the photolysis of 2-pentanone vapor. J. Am. Chem. Soc., 1964, 86, 3602-3605.
4. Yang, N. C.; Yang, D. H. Photochemical reactions of ketones in solution. J. Am. Chem. Soc., 1958, 80, 2913-2914.
5. Wagner, P. J. Type II Photoelimination and photocyclization of ketones. Acc. Chem. Res., 1971, 4, 168-177.
6. Wagner, P. J. Chemistry of excited triplet organic carbonyl compounds. Topics Curr. Chem., 1976, 66, 1-52.
7. Wagner, P. J. 1, 5-Biradicals and five-membered rings generated by α-hydrogen abstraction in photoexcited ketones. Acc. Chem. Res., 1989, 22, 83-91.
8. Wagner, P. J.; Park, B. S. Photoinduced hydrogen atom abstraction by carbonyl compounds, In: Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; pp. 227-366.
9. Wagner, P. J. Norrish type II photoelimination of ketones: Cleavage of 1, 4-biradicals formed by α-hydrogen abstraction. CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M.; Song, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; pp. 443-449.
10. Horspool, W. M.; Lenci, F. CRC Handbook Of Organic Photochemistry And Photobiology, 2nd ed.; CRC Press: LLC. Boca Raton, 2004; pp. 1435-1463.
11. Nagaoka, A.; Nagashima, U. Intramolecular proton-transfer in various electronic states of ortho-hydroxybenzaldehyde. Chem. Phys., 1989, 136, 153-163.
12. Sengupta, P. K.; Kasha, M. Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin. Chem. Phys. Lett., 1979, 68, 382-385.
13. Gourrierec, D. L.; Ormson, S. M.; Brown, R. G. Excited-state intramolecular proton transfer. Part 2: ESIPT to oxygen. Prog. React. Kinet., 1994, 19, 211-221.
14. Maedor, M. A.; Wagner, P. J. 2-Indanol formation from photocyclization of alpha.-arylacetophenones. J. Am. Chem. Soc., 1983, 105, 4484-4486.
15. Pappas, S. P.; Zehar R. D. Heavy-atom effects on the stereochemistry of photoabstraction-cyclization in a carbonyl system. J. Am. Chem. Soc., 1971, 93, 7112-7113.
16. Lappin, G. R.; Zannucci J. S. Photolysis of 2-(benzyloxy)-4-(dodecyloxy)benzophenone and 2-isopropoxy-4-methoxybenzophenone. J. Org. Chem., 1971, 36, 1808-1811.
17. Park, K. K.; Han, I. K.; Park, J. W. Photochemical synthesis of cyclophanes containing tethered benzofuran rings. J. Org. Chem., 2001, 66, 6800-6802.
18. Stermitz, F. R.; Wei, C. C. Photochemistry of aromatic N-heterocycles. IV. McLafferty rearrangement and type II photocleavage comparisons in new system 2-substituted quinolines. J. Am. Chem. Soc., 1969, 91, 3103-3104.
19. Howard, A. J. C.; Samson, M. K. Intramolecular hydrogen abstraction in ketone photochemistry: The first examples of α-hydrogen abstraction. J. Chem. Soc. Chem. Commun., 1987, (21), 1673-1674.
20. Sato, Y.; Nakai, H.; Mizoguchi, T.; Hatanaka, Y.; Kanaoka, Y. Photochemistry of the phthalimide system. VII. Regioselective remote photocyclization. Examples of a photochemical macrocyclic synthesis with sulfide-containing phthalimides. J. Am. Chem. Soc., 1976, 98(8), 2349-2351.
21. DeCosta, D. P.; Bennett, A. K.; Pincock, J. A. The Norrish Type II Photofragmentation of esters induced by intramolecular electron transfer. J. Am. Chem. Soc., 1999, 121, 3785-3786.
22. Yarchak, M. L.; Dalton, J. C.; Saunders W. H. Mechanisms of elimination reactions. XX. Stereochemistry of photoeliminations from some cyclic phenylacetates. J. Am. Chem. Soc., 1973, 95, 5224-5227.
23. Henin, F.; Muzart, J.; Pete, J. P.; Mboungoumpassi, A.; Rau, H. Enantioselective protonation of a simple enol: Aminoalcohol-catalyzed ketonization of a photochemically produced 2-methylinden-3-ol. Angew. Chem., Int. Ed. Engl., 1991, 30, 416-418.
24. Henin, F.; Mboungoumpassi, A.; Muzart, J.; Pete, J. P. Photoreactivity of alpha-tetrasubstituted arylketones: Production and asymmetric tautomerization of arylenols. Tetrahedron, 1994, 50, 2849-2864.
25. Wagner, P. J.; Scheve, B. J. Competing triplet reactions in azidoketones. J. Am. Chem. Soc., 1979, 101, 378-383.
26. Cottier, L.; Remy, G.; Descotes, G. Photochemical synthesis of o-vinyl glycosides and their transformation into c-branched sugars. Synthesis, 1979, 711-712.
27. Chen S.; Patrick B. O.; Scheffer J. R. Enantioselective photochemical synthesis of a simple alkene via the solid state ionic chiral auxiliary approach. J. Org. Chem., 2004, 69, 2711-2718.
28. Gao, L. J.; Zhao, T. Z.; Han, G. D. A novel method for the synthesis of a C/Dring synthon of vitamin D derivatives from hyodeoxycholic acid. Tetrahedron Lett., 1999, 40, 131-132.
29. Hilgeis, G.; Scharf, H. D. Synthese von 5ʹ-Androstan-3, 17-dion aus cholsäure liebigs. Ann. Chem., 1985, (7), 1343-1498.
30. Breslow R. Biomimetic control of chemical selectivity. Acc. Chem. Res., 1980, 13, 170-177.
31. Breslow, R.; Rothbard, J.; Herman, F.; Rodriguez, M. L. Remote functionalization reactions as conformational probes for flexible alkyl chains. J. Am. Chem. Soc., 1978, 100, 1213-1218.
32. Wiedenfeld D.; Breslow, R. Directed formation of carbon-bromine and carbon-sulfur bonds by tandem radical chain reactions. J. Am. Chem. Soc., 1991, 113, 8977-8978.
33. Breslow, R.; Baldwin, S.; Flechtner, T.; Kalicky, P.; Liu, S.; Washburn, W. Remote oxidation of steroids by photolysis of attached benzophenone groups. J. Am. Chem. Soc., 1973, 95, 3251-3262.
34. Wife, R. L.; Prezant, D.; Breslow, R. Concerning the regiospecificity and stereospecificity of steroid functionalization by photolysis of attached benzophenone esters. Tetrahedron Lett., 1976, 17, 517-520.
35. Jung, E.; Johnson, T. W. First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols. Org. Lett., 1999, 1, 1671-1674.
36. Wagner, P. J.; Liu, K. C.; Noguchi, Y. Monoradical rearrangements of the 1, 4-biradicals involved in Norrish type II photoreactions. J. Am. Chem. Soc., 1981, 103, 3837-3841.
37. Caldwell, R. A.; Gupta, S. C. Absence of conformational dependence of Norrish II biradical lifetimes. J. Am. Chem. Soc., 1989, 111, 740-742.
38. Berar, S.; Jindal, P.; Berar, U.; Bhatia, R.; Chaudhary, A.; Kamboj, R. C. Photochemical and thermal transformations of some diallyl-1-benzoylcyclopropanes. J. Ind. Chem. Soc., 2014, 91, 2271-2282.
39. Kraus, G. A.; Wu, Y. 1, 5-and 1, 9-Hydrogen atom abstractions. Photochemical strategies for radical cyclizations. J. Am Chem. Soc., 1992, 114, 8705-8707.
40. Zimmerman, H. E.; Cowley, B. R.; Tseng, C. Y.; Wilson, J. W. A general theory of photochemical reactions. VII. Mechanisms of epoxy reactions. J. Am. Chem. Soc., 1964, 86, 947-948.
41. Kamboj, R. C.; Jindal, P.; Kumar, D.; Khullar, S.; Mandal, S. K. Synthesis of some 'benzofurooxepines' derivatives via [3+2] cycloaddition of epoxide with tethered alkyne: A photochemical approach. J. Photochem. Photobiol. A, 2014, 278, 31-38.
42. Cookson, R. C.; Rogers, N. R. A new photochemical reaction of α, β-unsaturated ketones. J. Chem. Soc., Chem. Comm., 1972, (13), 809-810.
43. Cereghetti, M.; Wehrli, H.; Schaffner, K.; Jeger, O. Über steroide und sexualhormone. 212. Mitteilung. Photochemische Umwandlungen von 20-ketopregnan-verbindungen. Helv. Chim. Acta., 1959, 42, 2122-2140.
44. Cereghetti, M.; Wehrli, H.; Schaffner, K.; Jeger, O. Über Steroide und Sexualhormone 216. Mitteilung. Zur Darstellung und Konfigurationsbestimmung der 20-Hydroxy-18, 20-cyclo-pregnan-verbindungen. Helv. Chim. Acta., 1960, 43, 347-354.
45. Iriarte, J.; Schaffner, K.; Jeger, O. Photochemische Reaktionen. 22. Mitteilung. UV.-Bestrahlung von 11-Oxo-Steroiden III. Zur Beeinflussung der (11 19)-Cyclization durch sterische Faktoren. Helv. Chim. Acta., 1963, 46, 1599-1609.
46. Iriarte, J.; Schaffner, K.; Jeger, O. Photochemische Reaktionen. 28. Mitteilung [1]. UV.-Bestrahlung von 11-Oxo-Steroiden IV. 3, 20-Di-äthylendioxy-11-oxo-C-nor-5ʹ-pregnan. Helv. Chim. Acta., 1964, 47, 1255-1264.
47. Jeger, O.; Schaffner, K. Photochemische umwandlungen von carbonyl verbindungen. Chem. Week. Blad., 1964, 60, 389.
48. Crowley, K. J. The synthesis of cyclobutenes by Photoisomerisation. Proc. Chem. Soc., 1962, 334.
49. Srinivasan, J. Kinetics of the photochemical dimerization of olefins to cyclobutane derivatives. I. Intramolecular addition. J. Am. Chem. Soc., 1962, 84, 4141-4145.
50. Hasegawa, T.; Ohkanda, J.; Kobayashi, M. Unusual substituent effect by the α-acetyl group on the type II photoreaction of valerophenones: Strong wavelength dependence of quantum yields. J. Photochem. Photobiol. A: Chem., 1992, 64, 299-230.
51. Hagiwara, Y.; Mesch, R. A.; Kawakami, T.; Okazaki, M.; Jockusch, S.; Li, Y.; Turro, N. J.; Willson, C. G. Design and synthesis of a photoaromatizationbased two-stage photobase generator for pitch division lithography. J. Org. Chem., 2013, 78, 1730-1734.
52. Jindal, P.; Sharma, G.; Arora, R.; Kamboj, R. C. Solution-phase photochemical transformation of 2-aroylbenzofurans: addition-elimination mechanism. Res. Chem. Intermed., 2015, 41, 4465-4476.
53. Mazzocchi, P. H.; Jameson, C. W.; Nishiyama, T.; De Camp, A. Competitive type II eliminations in aliphatic imides. Tetrahedron Lett., 1980, 21, 989-992.
54. Margerum, J. D.; Miller, L. J.; Saito, E.; Brown, M. S.; Mosher, H. S.; Hardwick, R. Phototropism of ortho-nitrobenzyl derivatives. J. Phys. Chem., 1962, 66, 2434-2438.
55. Margerum, J. D. Transient photodecarboxylation intermediates. J. Am. Chem. Soc., 1965, 87, 3772-3773.
56. Cohen, M. D.; Schmidt, G. M. J.; Flavian, S. Topochemistry. Part VI. Experiments on photochromy and thermochromy of crystalline anils of salicylaldehydes. J. Chem. Soc., 1964, (0), 2041-2051.
57. Cohen, M. D.; Hirshberg, D. Y.; Schmidt, G. M. J. Opochemistry. Part VII. The photoactivity of anils of salicylaldehydes in rigid solutions. J. Chem. Soc., 1964, 2051-2060.
58. Stermitz, F. R.; Wei, C. C. Photochemistry of aromatic N-heterocycles. IV. McLafferty rearrangement and type II photocleavage comparisons in a new system. 2-Substituted quinolines. J. Am. Chem. Soc., 1969, 91, 3103-3104.
59. Morrill, J. R.; Bennett, R. G. Influence of intramolecular hydrogen bonding on electronic de-excitation in amidophenylbenzotriazoles. J. Chem. Phys., 1965, 43, 1410-1414.
60. Becker, R. S.; Richey, W. F. Photochromic anils. Mechanisms and products of photoreactions and thermal reactions. J. Am. Chem. Soc., 1967, 89, 1298-1302.
61. Wessig, P.; Mühling, O. A new photochemical route to cyclopropanes. Angew. Chem. Int. Ed., 2001, 40, 1064-1065.
62. Muehli, O.; Wessig, P. Stereoselective synthesis of cyclopropanes based on a 1, 2-chirality transfer. Chem. Eur. J., 2008, 14, 7951-7960.
63. Manh, D. D. K.; Ecoto, J.; Fetizon, M.; Colin, H.; Diez-Masa, J. C. A new approach to spirosesquiterpenes of the acorane family. J. Chem. Soc. Chem. Commun., 1981, (18), 953-955.
64. Kanaoka, Y.; Okajima, H.; Hatanaka, Y.; Terashima, M. Syntheses of bicyclocaprolactam systems by the photo-ring-expansion of N-substituted succinimides. Hetetrocycles, 1978, 11, 455-460.
65. Gupta, S. C.; Thakur, M.; Sharma, S.; Berar, U.; Berar, S.; Kamboj, R. C. Synthesis of spiropyrans: H-abstractions in 3-cycloalkenyloxybenzopyrans. Beilstein J. Org. Chem., 2007, 3, 14.
66. Jindal, P.; Kamboj, R. C. A green synthesis of some novel spirocyclics: A norrish type II process in 3-cyclohexenyloxy-2-(furans-3-yl)-4H-chromen-4-ones. Int. J. Chem. Chem. Eng., 2013, 3, 55-60.
67. Herrera, A.; Rondón, M.; Suárez, E. Stereocontrolled photocyclization of 1, 2-diketones applied to carbohydrate models: A new entry to C-ketosides. Synlett, 2007, 1851-1856.
68. Herrera, A.; Rondón, M.; Suárez, E. Stereocontrolled photocyclization of 1, 2-diketones: Application of a 1, 3-acetyl group transfer methodology to carbohydrates. J. Org. Chem., 2008, 73, 3384-3391.
69. Alvarez-Dorta, D.; Leon, E. I.; Kennedy, A. R.; Riesco-Fagundo, C.; Suárez, E. Sequential norrish type II photoelimination and intramolecular aldol cyclization of 1, 2-Diketones in carbohydrate systems: Stereoselective synthesis of cyclopentitols. Angew. Chem. Int. Ed., 2008, 47, 8917-8919.
70. AlvarezDorta, D.; León, E. I.; Kennedy, A. R.; Martín, A.; Pérez-Martín, I.; Riesco-Fagundo, C.; Suárez, E. Photochemistry of α-diketones in carbohydrates: Anomalous norrish type II photoelimination and norrish-yang photocyclization promoted by the internal carbonyl group. Chem. Eur. J., 2014, 20, 2663-2671.
71. Descotes, G. Acetal photoreactivity in the heterocyclic and glycoside series. Bull. Soc. Chim. Belg., 1982, 91, 974.
72. Descotes, G. Synthetic saccharide photochemistry. Top. Curr. Chem., 1990, 154, 39-76.
73. Couture, A.; Hoshino, M.; Mayo, P. D. Thione photochemistry: Cyclopropanethiol formation from arylalkyl thiones. JCS Chem. Comm., 1976, (4), 131-132.
74. Muehli, O.; Wessig. P. Stereoselective synthesis of cyclopropanes based on a 1, 2-chirality transfer. Chem. Eur. J., 2008, 14, 7951-7960.
75. Yoshioka, M.; Miyazoe, S.; Hasegawa, T. Photochemical reaction of 3-hydroxy-1-(o-methylaryl)alkan-1-ones: Formation of cyclopropane-1, 2-diols and benzocyclobutenols through α-and β-hydrogen abstractions. J. Chem. Soc., Perkin Trans., 1993, 1, 2781-2786.
76. Cormier, R. A.; Schreiber, W. L.; Agosta, W. C. Photochemical rearrangements of β-methylene ketones. J. Am. Chem. Soc., 1973, 95, 4873-4884.
77. Cormier, R. A.; Agosta, W. C. Singlet biradical intermediates in the photochemistry of β-methylene ketones. J. Am. Chem. Soc., 1974, 96, 618-620.
78. Roth, H. J.; El Raie, M. H. Photocyclisierung von 3-aminoketonen zu 2-aminocyclopropanolen. Tetrahedron Lett., 1970, 11, 2445-2446.
79. Abdul-Baki, A.; Rotter, F.; Schrauth, T.; Roth, H. J. Versuche zur photochemischen synthese ephedrinähnlicher verbindungen, III photocyclisierung von 3-alky laminopropiophenonen zu 2-alkylamino-cyclopropanolen-(1) und deren isomerisierung. Arch. Pharm., 1978, 311, 341-345.
80. Wagner, P. J. Solvent effects on type II photoelimination of phenyl ketones. J. Am. Chem. Soc., 1967, 89, 5898-5901.
81. Wagner, P. J.; Kochevar, I. E.; Kemppainen, A. E. Type II photoprocesses of phenyl ketones. Procedures for determining meaningful quantum yields and triplet lifetimes. J. Am. Chem. Soc., 1972, 94, 7489-7494.
82. Weigel, W.; Wagner, P. J. Photocyclization to cyclopropanols and exciplex emission of â-arylpropiophenones. J. Am. Chem. Soc., 1996, 118, 12858-12859.
83. Timpe, H. J.; Rakhmankulov, D. L.; Zlotzkij, S. S.; Akhmetkhanova, F. M. Preparation of cyclopropanols via photoinduced β-hydrogen abstraction in 5-acyl 1, 3-dioxanes. J. Photochem. Photobiol. A: Chem., 1993, 74, 31-35.
84. Chen, S.; Patrick, B. O.; Scheffer, J. R. Enantioselective photochemical synthesis of a simple alkene via the solid state ionic chiral auxiliary approach. J. Org Chem., 2004, 69, 2711-2718.
85. Lindemann, U.; Wulff-Molder, D.; Wessig, P. Diastereoselective synthesis of 3-hydroxy-3-phenyl-cyclobutanoic derivatives by photocyclization. J. Photochem. Photobiol. A: Chem., 1998, 119, 73-83.
86. Matsui, T.; Komatsu, A.; Moroe, T. Photochemistry of isopulegone. Bull. Chem. Soc. Jpn., 1967, 40, 2204.
87. Sheehan, J. C.; Wilson, R. M. Stereospecific synthesis and electronic absorption properties of cis-and trans-4-acetoxyisopulegone. J. Am. Chem. Soc., 1967, 89, 3457-3462.
88. Cookson, R. C.; Hudec, J.; Szabo, A.; Usher, G. E. The optical and photochemical properties of methylisopulegone. Tetrahedron, 1968, 24, 4353-4357.
89. Padwa, A.; Alexander, E. Photochemical formation of a substituted bicyclo[1. 1. 1]pentane. Izw Akad Nauk SSSR Ser Khim, 1967, 89, 6376-6377.
90. Padwa, A.; Shefter, E.; Alexander, E. The correlation of the crystal and molecular structure with the nuclear magnetic resonance spectrum of a bicycle [1. 1. 1] pentane derivative. J. Am. Chem. Soc., 1968, 90, 3717-3721.
91. Padwa, A.; Alexander, E.; Niemcyzk, M. Photochemical transformations of small ring carbonyl compounds. XIX. Photochemistry of benzoylcyclobutanes. J. Am. Chem. Soc., 1969, 91, 456-460.
92. Padwa, A.; Eisenberg, W. Photochemical transformation of small ring carbonyl compounds. XXV. Photochemical synthesis of the tricycle [3. 2. 0. 026] heptane system. J. Am. Chem. Soc., 1970, 92, 2590-2591.
93. Dijksman, W. C.; Verboom, W.; Reinhoudlt, D. N.; Hale, C. G.; Harkema, S.; Van Hummel, G. J. Novel application of the "t-aminoeffect" in heterocyclic chemistry; synthesis of 1-alkylindoles. Teterahedron Lett., 1984, 25, 2055-2058.
94. Osuka, A. Photochemistry of epoxyquinones. 6. Norrish type II photoreaction of 2, 3-dihydro-2, 3-epoxy-1, 4-naphthoquinone. J. Org. Chem., 1982, 47, 3131-3139.
95. Ceregetti, M.; Wehrili, H.; Schaffner, K.; Jeger, O. Über Steroide und sexualhormone. 212. Mitteilung. photochemische umwandlungen von 20-ketopregnan-verbindungen. Helv. Chim. Acta., 1959, 42, 2122-2140.
96. Ceregetti, M.; Wehrili, H.; Schaffner, K.; Jeger, O. Über Steroide und Sexualhormone 216. Mitteilung. Zur Darstellung und Konfigurationsbestimmung der 20-Hydroxy-18, 20-cyclo-pregnan-verbindungen. Helv. Chim. Acta., 1960, 43, 354-366.
97. Plassman, P. S.; Nelson, P. H.; Boyle, P. H.; Cruz, A.; Iriarte, J.; Crabbe, P.; Edwards, J. A.; Fried, J. H. Photochemical cycloadducts. IV. Photochemical addition of olefins and acetylene to 3β-acetoxypregna-5, 16-dien-20-one. J. Org. Chem., 1969, 34, 3779-3784.
98. Botoshansky, M.; Braga, D.; Kaftory, M.; Maini, L.; Patrick, B. O.; Schefferc, J. R.; Wang, K. Molecular mechanics-assisted crystal engineering of solid state photoreactions: Application to the yang photocyclization of β-1-norbornylacetophenone derivatives. Tetrahedron Lett., 2005, 46, 1141-1144.
99. Mortko, C. J.; Dang, H.; Campos, L. M.; García-Garibay, M. A. H-abstraction prevails over γ-cleavage in the solution and solid state photochemistry of cis-2, 6-di(1-cyclohexenyl) cyclohexanone. Tetrahedron Lett., 2003, 44, 6133-6136.
100. Koshima, H.; Fukano, M.; Uekusa, H. Diastereospecific photocyclization of a isopropylbenzophenone derivative in crystals and the morphological changes. J. Org. Chem., 2007, 72, 6786-6791.
101. Creary, X.; Hinckley, J.; Kraft, C.; Genereux, M. Enantioselective conjugate addition nitro-mannich reactions: Solvent controlled synthesis of acyclic anti and syn γ-nitroamines with three contiguous stereocenters. J. Org. Chem., 2011, 76, 2062-2071.
102. Ignatenko, V. A.; Tochtrop, G. P. Approach for expanding triterpenoid complexity via divergent norrish-yang photocyclization. J. Org. Chem., 2013, 78, 3821-3831.
103. Turro. N. J.; Lee, T. J. Molecular photochemistry. XX. Intramolecular photoreduction of alkyl a-diketones. J. Am. Chem. Soc., 1969, 91, 5651-5652.
104. Anderson, J. R.; Briant, C. E.; Edwards, R. L.; Mabelis, R. P.; Poyser, J. P.; Spencer, H.; Whalley, A. J. S.; Freer, A. A. Corrigenda. J. Chem. Soc. Chem. Commun., 1986, (12), 984.
105. Paquette, L. A.; Sugimura, T. Enantiospecific total synthesis and absolute configurational assignment of (-)-punctatin A (antibiotic M95464). J. Am. Chem. Soc., 1986, 108, 3841-3842.
106. Sugimura, T.; Paquette L. A. Enantiospecific total synthesis of the sesquiterpene antibiotics (-)-punctatin A and (+)-punctatin D. J. Am. Chem. Soc., 1987, 109, 3017-3024.
107. Gudmundsdottir, A. D.; Lewis, T. J.; Randall, L. H.; Scheffer, J. R.; Rettig, S. J.; Trotter J.; Wu, C. H. Geometric requirements for hydrogen abstractability and 1, 4-biradical reactivity in the norrish/yang type II reaction: Studies based on the solid state photochemistry and x-ray crystallography of medium-sized ring and macrocyclic diketones. J. Am. Chem. Soc., 1996, 118, 6167-6184.
108. Arnould, J. C.; Pete, J. P. Photolyse D+ alcoxycyclohexanones. Tetrahedron Lett., 1972, 13, 2415-2418.
109. Wessig, P.; Schwarz, J. Enantioselective preparation of (2R)-and (2S)-azetidine-2-carboxylic acids. Helv. Chim. Acta., 1998, 81, 1803-1814.
110. Pedrosa, R.; Andres, V.; Nieto, J.; Pozo, S. D. Diastereoselective yang photocyclization reactions in solution. Synthesis of enantiopure azetidin-3-ol derivatives. J. Org. Chem., 2005, 70, 1408-1416.
111. Bach, T.; Aechtner, T.; Neumüller, B. Enantioselective Norrish-Yang Cyclization Reactions of N-(Δ-Oxo-Δ-phenylalkyl)-Substituted Imidazolidinones in Solution and in the Solid State. Chem. Eur. J., 2002, 8, 2464-2475.
112. Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. Photochemical reactions of Δ-oxo amides. Norrish type II reactions via zwitterionic intermediates. J. Am. Chem. Soc., 1983, 105, 1958-1964.
113. Griesbeck, A. G.; Heckroth, H. Reversible diastereoselective photocyclization of phenylglyoxylamides of Δ-amino acid methyl esters to 3-hydroxy δ-lactams. Synlett, 2002, (1), 131-133.
114. Henery-logan, K. R.; Chen, C. G. Synthesis of oxygen analogs of the penicillins. I. Photocyclization of 2-oxoamides to 3-carbomethoxy-6-hydroxypenams. Tetrahedron Lett., 1973, 14, 1103-1104.
115. Blanc, S. L.; Pete, J. P.; Piva, O. New access to spiranic δ-lactams. Tetrahedron Lett., 1992, 33, 1993-1996.
116. Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. Photochemical reactions of N, N-disubstituted. alpha.-oxoamides. J. Org. Chem., 1978, 43(3), 419-422.
117. Aoyama, H.; Hasegawa, T.; Omote, Y. Solid state photochemistry of N, Ndialkyl-. alpha.-oxoamides. Type II reactions in the crystalline state. J. Am. Chem. Soc., 1979, 101, 5343-5347.
118. Wagner, P. J.; Kelso, P. A.; Kemppainen, A. E.; Richard, G.; Zepp, R. G. Type II photoprocesses of phenyl ketones competitive δ-H abstraction and the geometry of intramolecular hydrogen atom transfers. J. Am. Chem. Soc., 1972, 94, 7500-7506.
119. Wagner, P. J.; Meador, M. A.; Giri, B. P.; Scaiano, J. C. Photoreactivities of oalkoxy-and o-tert-butylphenyl ketones: A dramatic example of conformational inversion of selectivity. J. Am. Chem. Soc., 1985, 107, 1087-1088.
120. Wagner, P. J.; Giri, B. P.; Scaiano, J. C.; Ward, D. L.; Gabe, E.; Lee, F. L. Photocyclization of o-tert-butylbenzophenone. J. Am. Chem. Soc., 1985, 107, 5483-5490.
121. Zand, A.; Park, B. S.; Wagner, P. J. Conformational control of product ratios from triplet 1, 5-biradicals. J. Org. Chem., 1997, 62, 2326-2327.
122. Zand, A.; Park, B. S.; Wagner, P. J. Conformational control of product ratios from triplet 1, 5-biradicals. J. Org. Chem., 1997, 62, 2326-2327.
123. Seiler, M.; Schumacher, A.; Lindemann, U.; Barbosa, F.; Giese, B. Diastereoselective photocyclization to dihydroindolinols. Synlett, 1999, 10, 1588-1590.
124. Kravitz, J. I.; Margaretha, P.; Agosta, W. C. Novel photochemical reaction of 2-(2-alkynyl)acetophenones initiated by type II abstraction. Tetrahedron Lett., 1991, 32, 31-34.
125. Wagner, P. J.; Liu, K.; Noguchi, Y. Monoradical rearrangements of the 1, 4-biradicals involved in norrish type II photoreactions. J. Am. Chem. Soc., 1981, 103, 3837-3841.
126. Wessig, P.; Schwarz, J.; Wulff-Molder, D.; Reck, G. Photochemical preparation of tricyclic hydroxyketones by transannular cyclization of bridged 4-benzoylcyclohexanones. Monatshefte Chem., 1997, 128, 849-862.
127. Bergmark, W. R.; Barnes, C.; Clark, J.; Paparian, S.; Marynowski, S. Photoenolization with. alpha.-chloro substituents. J. Org. Chem., 1985, 50, 5612-5615.
128. Klán, P.; Zabadal, M.; Heger, D. 2, 5-Dimethylphenacyl as a new photo releasable protecting group for carboxylic acids. Org. Lett., 2000, 2, 1569-1571.
129. Wessig, P.; Teubner, J. Total synthesis of pterosines B and C via a photochemical key step. Synlett, 2006, (10), 1543-1546.
130. Wessig, P.; Muehling, O. Spin-center shift (SCS)-A versatile concept in biological and synthetic chemistry. J. Org. Chem., 2007, (14), 2219-2232.
131. Wessig, P.; Glombitza, C.; Müller, G.; Teubner J. Photochemical preparation of highly functionalized 1-indanones. J. Org. Chem., 2004, 69, 7582-7591.
132. De Mayo, P.; Suau, R. Photochemical synthesis. Part LVIII. A photochemical synthesis of (±)-cuparene. J. Chem. Soc. Perkin Trans., 1974, 1, 2559-2561.
133. De Mayo, P.; Suau, R. Photochemical synthesis. 57. Thione photochemistry. 16. Type II and homo-type II photoprocesses. Specific reactivity of upper and lower excited states of aralkyl thiones. J. Am. Chem. Soc., 1974, 96, 6807-6809.
134. Carless, H. A. J.; Swan, D. I.; Haywood, D. J. Stereoselective synthesis of tetrahydrofuran-3-ols by photochemical γ-hydrogen abstraction of γ-allyloxy-carbonyl compounds. Tetrahedron, 1993, 49, 1665-1674.
135. Araki, Y.; Arai, Y.; Endo, T.; Ishido, Y. Stereoselective photochemical cyclization of 3-O-benzyl-6-deoxy-1, 2-O-isopropylidene-α-D-xylohexofuranos-5-ulose derivatives. Chem. Lett., 1989, (18), 1.
136. Kraus, G. A.; Schwinden, M. D. Type II photocyclizations of carbohydrates. J. Photochem. Photobiol. A, 1991, 62, 241-244.
137. Lappin, G. R.; Zanucci, J. S. Photolysis of 2-(benzyloxy)-4-(dodecyloxy)benzophenone and 2-isopropoxy-4-methoxybenzophenone. J. Org. Chem., 1971, 36, 1808-1811.
138. Pappas, S. P.; Zehr Jr, R. D. Heavy-atom effects on the stereochemistry of photoabstraction-cyclization in a carbonyl system. J. Am. Chem. Soc., 1971, 93, 7112-7113.
139. Wagner, P. J.; Meador, M. A.; Park, B. S. The photocyclization of o-alkoxy phenyl ketones. J. Am. Chem. Soc., 1990, 112, 5199-5211.
140. George, A.; Kraus, P. J.; Thomas, S. An approach to aflatoxins using type II photocyclization reactions. Tetrahedron Lett., 1990, 31, 1819-1822.
141. Horaguchi, T.; Tsukada, C.; Hasegawa, E.; Shimizu, T.; Suzuki, T.; Tanemura, K. Photocyclization reactions. Part 2 Synthesis of dihydrobenzofuranols using photocyclization of ethyl 2-formylphenoxyacetates and ethyl 2-acetylphenoxyacetates. J. Het. Chem., 1991, 28, 1273-1280.
142. Pappas, S. P.; Pappas, B. C.; Backwell, J. E. Photocyclization of methyl obenzyloxyphenylglyoxylate. J. Org. Chem., 1967, 32, 3066-3069.
143. Yamada, A.; Iwaoka, Y.; Fujita, S.; Tsuzuki. Tetraalkylammoniumtemplated stereoselective Norrish-Yang cyclization. Org. Lett., 2013, 15, 5994-5997.
144. Thakur, M.; Berar, U.; Berar, S.; Gupta, S. C.; Kamboj, R. C. Photoreorganisation of 1, 5-bis (alkoxy)-2, 4-dibenzoylbenzenes: γ-H abstraction leading to dihydrobenzofurans. Ind. J. Heterocycl. Chem., 2008, 17, 257-262.
145. Šebej, P.; Lim, B. H.; Park, B. S.; Givens, R. S.; Klán, P. Monofluorovinyl tosylate: A useful building block for the synthesis of terminal vinyl monofluorides. Org. Lett., 2011, 13, 644-647.
146. Kozluk, T.; Cottier, L.; Descotes, G. Syntheses photochimiques de dioxa-1, 6 spiro[4. 5]decanes pheromones de Paravespula vulgaris L. Tetrahedron, 1981, 37, 1875-1880.
147. Kraus, G. A.; Chen, L. A total synthesis of racemic paulownin using a type II photocyclization reaction. J. Am. Chem. Soc., 1990, 112, 3464-3466.
148. Alvarez-Dorta, D.; Leon, E. I.; Kennedy, A. R.; Riesco-Fagundo, C.; Suárez, E. Sequential norrish type II photoelimination and intramolecular aldol cyclization of 1, 2-diketones in carbohydrate systems: Stereoselective synthesis of cyclopentitols. Angew. Chem. Int. Ed., 2008, 47, 8917-8919.
149. Dorta, D. A.; León, E. I.; Kennedy, A. R.; Martín, A.; Pérez-Martín, I.; Riesco-Fagundo, C.; Suárez, E. Photochemistry of α-diketones in carbohydrates: Anomalous norrish type II photoelimination and Norrish-Yang photocyclization promoted by the internal carbonyl group. Chem. Eur. J., 2014, 20, 2663-2671.
150. Haber, H.; Buchholz, H.; Sukale, R.; Henning, H. G. Photochemie von aminoketonen. VII. Eine diastereoselektive Synthese von 3-Hydroxy-prolinen. J. Prakt. Chem., 1985, 327, 51-62.
151. Walther, K.; Kranj, U.; Henning, H. G. Photochemie von aminoketonen. X. Darstellung und diastereoselektive photocyclisierung von N-(-Benzoylethyl)-N-tosyl-glycinamiden. J. Furpraktische Chem., 1987, 329, 859-870.
152. Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Asymmetric synthesis of 3-hydroxyprolines by photocyclization of N-(2-Benzoylethyl)glycinamides. Helv. Chim. Acta., 1994, 77, 829-837.
153. Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Chiralitäts-memory-effect in der Photochemie. Angew. Chem., 1999, 111, 2722-2724.
154. Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Memory of chirality in photochemistry. Angew. Chem. Int. Ed., 1999, 38, 2586-2587.
155. Sinicropi, A.; Barbosa, F.; Basosi, R.; Giese, B.; Olivucci, M. Mechanism of the norrish-yang photocyclization reaction of an alanine derivative in the singlet state: Origin of the chiral-memory effect. Angew. Chem., 2005, 117, 2442-2445.
156. Sinicropi, A.; Barbosa, F.; Basosi, R.; Giese, B.; Olivucci, M. Mechanism of the norrish-yang photocyclization reaction of an alanine derivative in the singlet state: Origin of the chiral-memory effect. Angew. Chem. Int. Ed., 2005, 44, 2390-2393.
157. Wessig, P.; Legart, F.; Hoffmann, B.; Henning, H. G. Photochemie von aminoketonen, 14. synthese und transannulare photocyclisierung von 2-benzoyl-1, 4-bis(tosyl)piperazinen. Liebigs Ann. Chem., 1991, (10), 979-982.
158. Gramain, J. C.; Remuson, R.; Vallee-Goyet, D.; Guilhem, J.; Lavaud, C. Total synthesis and determination of structure of the pyrrolizidine alkaloid curassanecine. J. Nat. Prod., 1991, 54, 1062-1067.
159. Keck, G. E.; Boden, E. P.; Mabury, S. A. A useful wittig reagent for the stereoselective synthesis of trans-α, β-unsaturated thiol esters. J. Org. Chem., 1985, 50(5), 709-710.
160. Hasegawa, T.; Moribe, J. I.; Yoshioka, M. The photocyclization of N, Ndialkyl-oxo amides on silica gel. Bullchem. Soc. Jpn., 1988, 61, 1437-1439.
161. Yoshioka, M.; Nishizawa, K.; Arai, M.; Hasegawa, T. Photochemical reaction of 1-(o-methylphenyl)-2, 2-dimethyl 1, 3-diketones. J. chem. Soc. Perkin Trans I., 1991, (3), 541-545.
162. Hasegawa, T.; Arata, Y.; Mizuno, K. γ-versusδ-hydrogen abstraction in the photochemistry of α-alkyl β-oxoamides. J. Chem. Soc. Chem. Commun., 1983, (7), 395-396.
163. Dittami, J. P.; Xu, F.; Qi, H.; Martin, M. W.; Bordner, J.; Decosta, D. L.; Kiplinger, J.; Reiche, P.; Ware, R. Preparation of N-alkyl pyrrolidinones via photocyclization of γ-keto-α, β-unsaturated amides. Tetrahedron Lett., 1995, 36, 4197-4200.
164. Dittami, J. P.; Xu, F.; Qi, H.; Martin, M. W.; Bordner, J.; Decosta, D. L.; Kiplinger, J.; Reiche, P.; Ware, R. Preparation of N-alkyl pyrrolidinones via photocyclization of γ-keto-α, β-unsaturated amides. Tetrahedron Lett., 1995, 36, 4201-4204.
165. Griesbeck, G. A.; Peters, K.; Peters, E. M.; Schnering, H. G. V. Photo electron transfer induced macrocyclization of N-phthaloyl-ε-aminocarboxylic acids. Angew. Chem. Int. Ed., 1995, 34, 474-476.
166. Griesbeck, G. A.; Dipl.-Chem, A. H. Photochemie von N-phthaloyl-α-aminosäureestern: Ein neuer zugang zu β, γ-ungesättigten α-aminosäuren und dihydrobenzazepindionen. Angew. Chem., 1992, 104, 97-99.
167. Gramain, J. C.; Remuson, R.; Vallée, D. Intramolecular photoreduction of a α-keto esters total synthesis of (+-) isoretronecanol. J. Org. Chem., 1985, 50, 710-712.
168. Lappin, G. R.; Zannucci, J. S. Photolysis of 2-(benzyloxy)-4-(dodecyloxy) benzophenone and 2-(isopropoxy)-4-methoxybenzophenone. J. Org. Chem., 1971, 36, 1808-1811.
169. Wagner, P. J.; Laidig, G. Enol ether formation by disproportionation of the 1, 5-biradical intermediate in the photocyclization of o-isopropoxybenzophenone. Tetrahedron Lett., 1991, 32, 895-898.
170. Wessig, P. An efficient synthesis of bicyclic-turn dipeptides via a photochemical key step. Tetrahedron Lett., 1987, 40, 5987-5988.
171. Wu, J.; Zhang, W.; Wang, C. Synthesis of benzopyrrolizidinones by Norrish-Yang cyclization of 3-(acylmethyl)-2-alkylisoindol-1-ones. Synthesis, 2009, (11), 1821-1828.
172. Cindro, N.; Horvat, M.; Mlinariń-Majerski, K.; Griesbeck, A. G.; Basariń, N. Photoinduced homolytic C-H activation in N-(4-homoadamantyl)phthalimide. Beilstein J. Org. Chem., 2011, 7, 270-277.
173. Roth, H. J.; Schwartz, D.; Hundeshagen, G. Photoreactions of phthalimide mannich bases in methanol. Archiv. der Pharma., 1976, 309, 48-58.
174. Chesta, C. A.; Whitten, D. G. Photocyclization of. alpha.-keto amides in homogeneous solution and aqueous cyclodextrin media. The role of zwitterions and diradicals in photoinduced electron transfer reactions. J. Am. Chem. Soc., 1992, 114, 2188-2197.
175. Zhou, B.; Wagner, P. J. Long-range triplet H-abstraction. Photochemical formation of 2-tetralols from p-arylpropiophenones. J. Am. Chem. Soc., 1989, 111, 6196-6199.
176. Hornback, J. M.; Poundstone, M. L.; Vadlamani, B.; Graham, S. M.; Gabay, J.; Patton, S. T. Photochemical cyclization of o-methylphenyl 1, 3-diketones. J. Org. Chem., 1988, 53, 5597.
177. Yoshioka, M.; Nishizawa, K.; Arai, M.; Hasegawa, T. Photochemical reaction of 1-(o-methylphenyl)-2, 2-dimethyl 1, 3-diketones. J. Chem. Soc. Perkin Trans I, 1991, (3), 541-545.
178. Kokubo, K.; Kawahara, K.; Takatani, T.; Moriwaki, H.; Kawamoto, T.; Oshima, T. Conformational specificity in photoinduced intramolecular 1, 7-H abstraction of homonaphthoquinones with a spiro-linked dibenzocycloheptene ring. Org. Lett., 2000, 2(4), 559-562.
179. Kraus, G. A.; Wu, Y. Hydrogen atom abstraction reactions in organic synthesis: A formal total synthesis of podophyllotoxin. J. Org. Chem., 1993, 57, 2919-2922.
180. Makino, B.; Kawai, M.; Kito, K.; Yamamura, H.; Butsugan, Y. New physalins possessing an additional carbon-carbon bond from Physalis alkekengi var. francheti. Tetrahedron, 1995, 51, 12529-12538.
181. Carless, H. A. J.; Fekarurhobo, G. K. Photochemical-hydrogen abstraction as a route to tetrahydropyran-3-ols. Tetrahedron Lett., 1984, 25, 5943-5946.
182. Meador, M. A.; Wagner, P. J. Photocyclization of ε-(o-benzyloxyphenyl) acetophenone: Triplet state-H abstraction. J. Org. Chem., 1985, 50, 419-420.
183. Jahjah, R.; Gassama. A.; Bulach, V.; Suzuki, C.; Abe, M.; Hoffmann, N.; Martinez, A.; Nuzillard, J. C. Stereoselective triplet-sensitised radical reactions of furanone derivatives. Chem. Eur. J., 2010, 16, 3341-3354.
184. Hayday, K.; McKelvey, R. D. An anomeric effect in photochemical hydrogen abstraction reactions of tetrahydropyranyl ethers. J. Org. Chem., 1976, 41, 2222-2223.
185. Kumar, R.; Yusuf, M. Photo-rearrangements of some 3-allyloxy-2-phenylchromones: Synthesis of vinyl substituted benzopyronopyranes. Org. Commun., 2008, 1, 39-47.
186. Thakur, M.; Berar, S.; Berar, U.; Arora, S.; Gupta, S. C.; Kamboj, R. C. Photo-transformations of 6-chloro-3-propargyloxy-2-aryl-4-oxo-4H-1-benzopyran: 1, 4-hydrogen abstraction in propargylethers. Tetrahedron, 2008, 64, 5168-5173.
187. Kamboj, R. C.; Berar, S.; Berar, U.; Thakur, M.; Gupta, S. C. Phototransformations of some 3-alkoxy-6-chloro-2-{(E)-1+-methyl-2+-phenylvinyl}chromones: A study of type-II and triene bichromophoric system. J. Photochem. Photobiol. A: Chem., 2009, 204, 122-128.
188. Kamboj, R. C.; Berar, U.; Berar, S.; Siddiqui, Z. N.; Gupta S. C. Photochemistry of 3-Alkoxychromones: Photocyclization of 2-aryl-6-chloro-3-{(thiophen-2-yl)methoxy}chromones. J. Braz. Chem. Soc., 2010, 21, 270-278.
189. Kamboj, R. C.; Kumar, D.; Sharma, G.; Arora, R. Photochemical transformations of some 2-(5-methylthiophen-2-yl)-3-[(naphthalen-2-yl)methoxy]-4Hchromen-4-ones involving type-II process. J. Chin. Chem., 2011, 29, 745-750.
190. Kamboj, R. C.; Arora, R.; Kumar, D.; Sharma, G. Photo-reorganization of 3-alkoxy-6-chloro-2-(thiophen-3-yl)-4H-chromen-4-ones: Regioselective cyclization via α-hydrogen abstraction. J. Photochem. Photobiol. A: Chem., 2011, 220, 124-133.
191. Kamboj, R. C.; Jindal, P.; Arora, R.; Chaudhary, A.; Khullar, S.; Mandal, S. K. Some novel photo-transformations in 4H-chromen-4-ones: Photolysis of 3-Propynyloxy-2-(thiophen-3-yl)-4H-chromen-4-ones. Chem. Sci. Rev. Lett., 2014, 3, 231-246.
192. Gupta, S. C.; Yusuf, M.; Arora, S.; Sharma, S.; Kamboj, R. C.; Dhawan, S. N. Photolysis of xylylbischromones. Tetrahedron, 2002, 58, 3095-3100.
193. Yusuf, M.; Kumar, R.; Gupta, S. C. Photochemical transformations of 1, 10-decylbischromones: Effect of spacer length (06-2102BP). Arkivoc, 2006, 15, 28-36.
194. Gupta, S. C.; Yusuf, M.; Arora, S.; Kamboj, R. C. Photolysis of xylylbischromones. Tetrahedron, 2003, 59, 3609-3612.
195. Griesbeck, G. Spin-Selectivity in photochemistry: A tool for organic synthesis. Synlett, 2003, 34(4), 451-472.
196. Wessig, P. CRC handbook of organic photochemistry and photobiology, 2nd ed.; Horspool, W.; Lenci, F., Eds.; 2004, 57, 1-20.
197. Wyss, C.; Batra, R.; Lehmann, C.; Sauer, S.; Giese, B. Selective photocyclization of glycine in dipeptides. Angew. Chem. Int. Ed. Engl., 1996, 35, 2529-2531.
198. Lindemann, U.; Reck, G.; Wulff-Molder, D.; Wessig, P. Photocyclization of 4-oxo-4-phenyl-butanoyl amines to α-lactams. Tetrahedron, 1998, 54, 2529-2544.
199. Wessig, P. An efficient synthesis of bicyclic α-turn dipeptides via a photochemical key step. Tetrahedron Lett., 1999, 40, 5987-5988.
200. Lindemann U.; Wulff-Molder D.; Wessig, P. Synthesis of ornithine lactams via diastereoselective photocyclization of 2-amino-4-oxo-4-phenyl-butanoyl amines. Tetrahedron: Asymmetry, 1998, 9, 4459-4473.
201. Griesbeck A. G.; Heckroth, H.; Schmickler, H. Regio-and stereoselective 1, 6-photocyclization of aspartic acid-derived chiral γ-ketoamides. Tetrahedron Lett., 1999, 40, 3137-3140.
202. Padwa, A.; Jacquez, M. N.; Schmidt, A. An approach toward azacycles using photochemical and radical cyclizations of N-alkenyl substituted 5-thioxopyrrolidin-2-ones. J. Org. Chem., 2004, 69, 33-45.
203. Wessig, P. Stereoselective synthesis of novel chimerical amino acids via a photochemical key step. Synlett, 1999, (9), 1465-1467.
204. Wessig, P.; Schwarz, J.; Lindemann, U.; Holthausen, M. C. Photochemical synthesis of 3, 4-dihydro-2H-1, 3-oxazin-4-ones. Synthesis, 2001, (8), 1258-1262.
205. Grilj, J.; Todorova, T. K.; Yi, C.; Vauthey, E.; Decurtins, S. A spectroscopic and computational study of a photoinduced cross-dehydrogenative coupling reaction of a stable semiquinone radical. Chem. Eur. J., 2012, 18, 13605-13608.
206. Stermitz, F. R.; Wei, C. C. Photochemistry of aromatic N-heterocycles. IV. McLafferty rearrangement and type II photocleavage comparisons in a new system. 2-substituted quinolines. J. Am. Chem. Soc., 1969, 91, 3103-3104.
207. Carless, H. A. J.; Mwesigye-Kibende, S. Intramolecular hydrogen abstraction in ketone photochemistry, the first example of β-hydrogen abstraction. J. Chem. Soc., Chem. Commun., 1987, (21), 1673-1674.
208. Cottet, F.; Cottier, L.; Descotes, G. Photocyclizations of aromatic ketoacetals as an approach to the synthesis of crombénine. Can. J. Chem., 1990, 68, 1251-1257.
209. Král, V.; Sessler, J. L.; Furuta, Král, H. V.; Sessler, J. L.; Furuta, H. Synthetic apphyrin-cytosine conjugates: Carriers for selective nucleotide transport at neutral pH. J. Am. Chem. Soc., 1992, 114, 8704-8705.
210. Newcomb, M.; Manek, M. B. Picosecond radical kinetics. Benzeneselenol as a fast radical trapping agent and rate constants for ring opening of the trans-(2-phenylcyclopropyl)carbinyl radical. J. Am. Chem. Soc., 1990, 112, 9662-9663.
211. Griesbeck, A. G.; Neudoerfl, J.; De Kiff, A. Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan. Beilstein. J. Org. Chem., 2011, 7, 518-524.
212. Kanaoka, Y. Photoreactions of cyclic imides. Examples of synthetic organic photochemistry. Acc. Chem. Res., 1978, 11, 407-413.
213. Kanaoka, Y.; Okajima, H.; Hatanaka, Y.; Terashima, M. Synthesis of bicyclocaprolactum system by the photo-ring-expansion of N-substituted succinimide. Heterocycles, 1978, 11, 455-460.
214. Richard B. Clark, M. D. "Epidural Anesthesia in Obstetrics" ASA Newsletter, 1998, 62, 17-19.
215. 2, 6] undecanamides. Angew chem. Int Ed., 1994, 33, 1979-1981.
216. Sowa, C. E.; Kopf, J.; Thiem, J. Syntheses of sugar-derived heterotricyclic lactams. J. Chem. Soc. Chem. Commun., 1995, (2), 211-212.
217. Sowa, C. E.; Stark, M.; Heidelberg, T.; Thiem, J. Novel approach to sugar derived spiroannelated. Heterocycles Synlett, 1996, (3), 227-228.
218. Kessar, S. V.; Singh, T.; Vohra, R. An interesting application of photocyclization in aporhoeadane alkaloid synthesis. Tetrahedron Lett., 1987, 28, 5323-5326.
219. Sakurai, N. N.; Iba, K.; Hamano, Y. I.; Sakamoto, M. Intramolecular photocyclization of 2-acylphenyl methacrylates: A convenient access to 4, 5-dihydro-1, 4-epoxy-2-benzoxepin-3(1H)-ones Benzo[c]-6, 8-dioxabicyclo [3. 2. 1] octan-7-ones. Helv. Chim. Acta, 2005, 88, 2603-2609.
220. Nishio, T.; Tabata, M.; Koyama, H.; Sakamoto, M. Photochemistry of N-(2-acylphenyl)-2-methylprop-2-enamides: Competition between photocyclization and long-range hydrogen abstraction. Helv. Chim. Acta, 2005, 88, 78-86.
221. Nishio, T.; Tabata, M.; Koyama, H.; Sasaki, D.; Sakamoto, M. A novel intramolecular photocyclization of N-(2-bromoalkanoyl) derivatives of 2-acylanilines via 1, 8-hydrogen abstraction. Helv. Chim. Acta, 2005, 88, 996-1003.
222. Hasegawa, T.; Yamazaki, Y. Regioselectivity in photocyclization of 2-(N, Ndialkylamino)-and 2-N-alkylanilino ethyl benzoylformates via remote proton transfer. Tetrahedron, 1998, 54, 12223-12232.
223. Hasegawa, T.; Miyata, K.; Ogawa, T.; Yoshihara, N.; Yoshioka, M. Remote photocyclization of (dibenzylamino) ethyl benzoylacetate. Intramolecular hydrogen abstraction through a ten-membered cyclic transition state. J. Chem. Soc., Chem. Commun., 1985, (6), 363-364.
224. Yamazaki, Y.; Miyagawa, T.; Hasegawa, T. Photocyclization of (alkythio) ethyl benzoyl acetates via remote proton transfer following charge transfer interaction between excited ketone carbonyl and thioether chromophore. J. Chem. Soc. Perkin Trans. 1, 1997, (20), 2979-2982.
225. Breslow, R. Biomimetic control of chemical selectivity. Acc. Chem. Res., 1980, 13, 170-177.
226. Winnik, M. A.; Lee, C. K.; Basu, S.; Saunders, D. S. Conformational analysis of hydrocarbon chains in solution carbon tetrachloride. J. Am. Chem. Soc., 1974, 96, 6182-6184.
227. Belmadoui, N.; Encinas, S.; Climent, M. J.; Gil, S.; Miranda, M. A. Intramolecular interactions in the triplet excited states of benzophenonethymine dyads. Chem.-A Eur. J., 2006, 12, 553-561.
228. Hasegawa, T.; Takashima, K.; Aoyama, H.; Yoshioka, M. Photochemical reactions of 4-oxocarboxylic esters: Remote H-abstraction and cis-trans isomerization. Bull. Chem. Soc. Jpn., 1992, 65, 3498-3500.
229. Hu, S.; Neckers, D. C. Photochemical reactions of alkoxy-containing alkyl phenyl glyoxylates remote hydrogen abstraction. J. Chem. Soc., Perkin Trans., 1997, 2, 1751-1754.
230. Hu, S.; Neckers, D. C. Photochemical reactions of sulfide-containing alkyl phenyl glyoxylates. Tetrahedron, 1997, 53, 7165-7180.
231. Hasegawa, T.; Ogawa, T.; Miyata, K.; Karakizawa, A.; Komiyama, M.; Nishizawa, K.; Yoshioka, M. Photocyclization of (β-dialkyamino)alkyl β-oxoesters via remote hydrogen transfer. J. Chem. Soc., Perkin Trans, 1990, 1, 901-905.
232. Kraus, G. A.; Zhang, W.; Wu, Y. 1, 12-Hydrogen atom abstraction reactions of γ-keto esters. Chem. Commun., 1996, (21), 2439-2440.
233. Andreu, B. F.; Sanchez, L.; Morera, I. M.; Camps, P.; Miranda, M. A. Efficient and selective photogeneration of cholesterol-derived radicals by intramolecular hydrogen abstraction in model dyads. Org. Lett., 2006, 8, 4597-4600.
234. Miranda, M. A.; Martínez, L. A.; Samadi, A.; Boscá, F.; Morera, I. M. Stereoselective intramolecular hydrogen abstraction by a chiral benzophenone derivative. Chem. Commun., 2002, (3), 280-281.
235. Boscá, F.; Andreu, I.; Morera, I. M.; Samadi, A.; Miranda, M. A. Chiral discrimination in the intramolecular abstraction of allylic hydrogens by benzophenonetriplets. Chem. Commun., 2003, (13), 1592-1593.
236. Abad, S.; Boscá, F.; Domingo, L. R.; Gil, S.; Pischel, U.; Miranda, M. A. Triplet reactivity and regio-/stereoselectivity in the macrocyclization of diastereomeric ketoprofen-quencher conjugates via remote hydrogen abstractions. J. Am. Chem. Soc., 2007, 129, 7407-7420.
237. Paris, C.; Encinas, S.; Belmadoui, N.; Climent, M. J.; Miranda, M. A. Photogeneration of 2-deoxyribonolactone in benzophenone-purine dyads. Formation of ketyl-C1ʹ biradicals. Org. Lett., 2008, 10, 4409-4412.
238. Pischel, U.; Abad, S.; Domingo, L. R.; Boscá, F.; Miranda, M. A. Angew. Chem., 2003, 115, 2635-2638.
239. Engelhardt, U.; Sarkar, A.; Linker, T. Efficient enantioselective total synthesis of (-) epipodophyllotoxin. Angew. Chem. Int. Ed., 2003, 42, 2487-2489.
240. Belmadoui, N.; Encinas, S.; Climent, M. J.; Gil, S.; Miranda, M. A. Intramolecular interactions in the triplet excited states of benzophenone-thymine dyads. Chem. Eur. J., 2005, 12, 553-561.
241. Lewandowska-Andralojc, F.; Kazmierczak, G. L.; Hug, G.; Hörner, B. Marciniak, photoinduced CC-coupling reactions of rigid diastereomeric benzophenone-methionine dyads. Photochem. Photobiol., 2013, 89, 14-23.
242. Breslow, R.; Corcoran, R. J.; Snider, B. B. Remote functionalization of steroids by a radical relay mechanism. J. Am. Chem. Soc., 1969, 91, 3083-3084.
243. Breslow, R.; Baldwin, S. W. Conversion of cholestanol to 12-oxocholestanol and to cholest-14-enol and-8(14)-enol by remote oxidation. J. Am. Chem. Soc., 1970, 92, 732-734.
244. Baldwin, J. E.; Bhatnagar, A. K.; Harper, R. W. Site-specific dehydrogenation of ring D in steroids. J. Chem. Soc. Chem. Commun., 1970, (11), 659-661.