Abstract
Photo-induced aromatic compounds in their excited singlet and triplet states undergo various chemical reactions. The triplet states of relatively long life times are involved in photochemical reactions in most cases. Photochemical reactions of aromatic compounds are mainly of eight types, isomerization, [2+2]- and [4+2]- cycloadditions, hydrogen abstraction and addition, electrocyclization, dimerization, oxidation, substitution and rearrangement reactions. The regio- and stereoselectivities of cycloaddition reactions of aromatic compounds with alkenes, allenes, dienes with numerous examples are highlighted. The photo-Fries rearrangement as well as the oxa- and aza-di-π-methane rearrangements are discussed in details. The photo-induced Diels–Alder reaction with mechanism and stereoselectivity are elaborated.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Wilzbach KE, Ritscher JS, Kaplan L (1967) J Am Chem Soc 89:1031
Kaplan L, Rausch DJ, Wilzbach KE (1972) J Am Chem Soc 94:8638
Wilzbach KE, Kaplan L (1965) J Am Chem Soc 87:4004
Malkin J (1992) Photophysical and photochemical properties of aromatic compounds. CRC Press, Boca Raton, Ann Arbor, p 141
Wilzbach KE. Kaplan L (1966) J Am Chem Soc 88:2066; Cornelisse J, Merritt VY. Srinivasan R (1973) J Am Chem Soc 95:6197; Gilbert A, Yianni P (1981) Tetrahedron 37:3275; Bryce- Smith D, Gilbert A, Orger BH (1966) J Chem Soc Chem Commun 512; Wagner-Jauregg T, (1980) Synthesis 165:769; Cornelisse J (1993) Chem Rev 93:615
Bryce- Smith D, Gilbert A, Orger BH (1974) J Chem Soc Chem Commun 334
Ferree W, Grutzner GB, Morrison H (1971) J Am Chem Soc 93:5502
Cornelisse J, Merritt VY, Srinivasan R (1973) J Am Chem Soc 95: 6197; Cornelisse J, Srinivasan R (1973) Chem Phys Lett 20:278
Weller A (1982) Z Phys Chem NF 133:93
Gilbert A (1980) Pure Appl Chem 52:2669; Bryce-Smith D, Foulger B, Forrester J, Gilbert A, Orger BH, Tyrrell HM (1980) J Chem Soc, Perkin Trans 1, 55; Cornelisse J, Srinivasan R (1973) Chem Phys Lett 20:278
Heine HG, Hartmann W (1975) Angew Chem 87: 708; Mattay J, Runsink J, Leisman H, Scharf HD (1982) Tetrahedron Lett 23:4919
Gilbert A, Taylor GN, Samsudin MWB (1980) J Chem Soc Perkin Trans 1, 869; Mattay J (1985) Tetrahedron 41:2405; Scharf HD, Mattay J (1977) Tetrahedron Lett 401
Gilbert A, Yianni P (1982) Tetrahedron Lett 4611; Idem (1981) Tetrahedron 37:3275
Osselton EM, Eyken CP, Jans AWH, Cornelisse J (1985) Tetrahedron Lett 26:1577
Mattay J, Leismann H, Scharf HD (1979) Chem Ber 112:577
Ohashi M, Tanaka Y, Yamada S (1976) J Che Soc Chem Commun 800
Ohashi M, Tanaka Y, Yamada S (1977) Tetrahedron Lett 3629
Cantrell TS (1977) J Org Chem 42:4238
Cantrell TS (1981) J Org Chem 46:2674
Bryce-Smith D, Foulgar BE, Gilbert A (1972) J Chem Soc Chem Commun 664
Yang NC, Libman J, Savitzky MF (1972) J Am Chem Soc 94:9226
Pac C, Sugioka T, Sakurai H (1972) Chem Lett 39; Kan K, Kai Y, Yasuoka N, Kasai N (1979) Bull Chem Soc Jpn 52:1634
Bryce-Smith D, Lodge JE (1963) J Chem Soc 695; Grovenstein E, Rao DV (1961) Tetrahedron Lett 148
Sasse WHF (1969) Aust J Chem 22:1257; Kowala C, Poppleton BJ, Sasse WHF (1976) Aust J Chem 29:1851; Sasse WHF, Collin PJ, Sugowdz G (1965) Tetrahedron Lett 3373
Davis PD, Neckers DC (1980) J Org Chem 45:456; Davis PD, Neckers DC, Blount JR (1980) J Org Chem 45:462
Morrison H (1979) Acc Chem Res 12:383; Pallmer M, Morrison H (1980). J Org Chem 45:798
Ohashi M, Tanaka Y, Yamada S (1977) Tetrahedron Lett 18:3629; Ferree W Jr, Grutzner JB, Morrison H (1971) J Am Chem Soc 93:5502
Padwa A, Goldstein S, Pulwer M (1982) J Org Chem 47:3893
Sedelmeir G, Fessner WD, Grund C, Spurr PR, Fritz H, Prinzbach H (1986) Tetrahedron Lett 27:1277
McCullough JJ, MacInnis WK, Lock CJL, Faggiani R (1982) J Am Chem Soc 104:4644
Yokoyama A, Mizuno K (2000) Org Lett 2:3457
Creed D, Caldwell RA, Ulrich MM (1978) J Am Chem Soc 100:5831
Gieseler A, Steckhan E, Wiest O, Knoch F (1991) J Org Chem 56:1405
Kjell DP, Sheridan RS (1985) J Photochem 28:205
Dopp D, Pies M (1987) J Chem Soc Chem Commun 1734
Ishii H, Imai Y, Hirano T, Maki S, Niwa H, Ohashi M (2000) Tetrahedron Lett 41:6467
McCullough JJ, Wu WS, Huang CW (1972) J. Chem Soc Perkin Trans 2:371
Lewis FD, Kalgutkar RS, Yang JS (2001) J Am Chem Soc 123:3878
Jones GB, Wright JM, Plourde G, Purohit AD, Wyatt JK, Hynd G, Fouad F (2000) J Am Chem Soc 122:9872
Kakiuchi K, Ue M, Yamaguchi B, Nishimoto A, Tobe Y (1991) Bull Chem Soc Jpn 64:3468
Bellus D (1971) Advances in photochemistry. Vol 8, Wiley, Chichester, p 109–159; Stenberg (1967) Org Photochem 1:127
Yoon YJ, Ko SH, Ko MK, Chae WK (2000) Bull Korean Chem Soc 21:901
Hagman HJ (1969) Tetrahedron 25:6015
Searle N (2003) Environmental effects on polymeric materials. In: Andrade A (ed) Plastic and environment. Wiley, pp 313–358
Coppinger GM, Bell ER (1966) J Phys Chem 70:3479
de Costa DP, Howell N, Pincock AL, Pincock JA, Rifai S (2000) J Org Chem 65:4698; Bogdanova A, Popik VV (2001) Org Lett 3:1885
Armesto D, Ortiz MJ, Romano S, Agarrabeita AR, Gallego MG, Ramos A (1996) J Org Chem 61:1459
Armesto D, Ramos A, Mayoral EP (1994) Tetrahedron Lett 35:3785; Armesto D, Ortiz MJ, Ramos A, Horspool WM, Mayoral EP (1994) J Org Chem 59:8115
Rio G, Berthelot J (1972) Bull Soc Chim Fr 822
Bowen EJ (1953) Discuss Faraday Soc 14:143; Foote CS (1968) Acc Chem Res 1: 104
Cowan DO, Drisko RL (1976) Elements of organic photochemistry. Plenum, New York
Bouas- Laurent H, Castellan A, Desvergne JP (1980) Pure Appl Chem 52:2633
Kowala C, Sugowdz G, Sasse WHF, Wunderlich JA (1972) Tetrahedron Lett 4721
Seliger BK, Sterns M (1969) J Chem Soc Chem Commun 978
Teitei T, Wells D, Spurling TH, Sasse WHF (1978) Aust J Chem 31:85; Teitei T, Wells D, Sasse WHF (1976) Aust J Chem 29:1783
Yamamoto M, Yoshikawa H, Gotoh T, Nishijima Y (1983) Bull Chem Soc Jpn 56:2531
Norman ROC, Coxon JM (1993) Principles of organic synthesis. Chapman & Hall, ELBS ed., Oxford, p 513
Nwokogu GC, Wong JW, Greenwood TD, Wolfe F (2000) Org Lett 2:2643
Ho TI, Ku CK, Liu RSH (2001) Tetrahedron Lett 42:715
Mangion D, Arnold DR, Cameron TS, Robertson KN (2001) J Chem Soc Perkin Trans 2:48
Chen QY, Li ZT (1993) J Chem Soc Perkin Trans 1:1705
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2017 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Dinda, B. (2017). Photochemistry of Aromatic Compounds. In: Essentials of Pericyclic and Photochemical Reactions. Lecture Notes in Chemistry, vol 93. Springer, Cham. https://doi.org/10.1007/978-3-319-45934-9_9
Download citation
DOI: https://doi.org/10.1007/978-3-319-45934-9_9
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-45933-2
Online ISBN: 978-3-319-45934-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)