Abstract
Cycloaddition reactions are the most useful pericyclic reactions in organic synthesis. These reactions are characterized by joining two π systems at their ends to form a ring compound through the formation of two new sigma bonds via the breaking of two π bonds, one from each π system in a concerted process. These reactions are classified according to the number of π electrons involved in each reacting component. The major classes are [π2+π2]-, [π4+π2]-, [π6+π2]-, [π8+π2]- and [π6+π4]-cycloaddition reactions. These are simply known as [2+2]-, [4+2]-, [6+2]-, [8+2]- and [6+4]-cycloaddition reactions. Among them, the Diels–Alder reactions and 1,3-dipolar cycloaddition reactions are widely applied in the synthesis of different types of polycyclic and heterocyclic compounds. Both these reactions are highly regio- and stereoselective and produce syn-addition products. Cheletropic reactions are a special group of cycloaddition or cycloreversion reactions, in which two sigma bonds are made or broken in the same atom of an electrophilic reacting component. The regio-, stereo- and enantioselectivities of the major classes of cycloaddition reactions and their wide applications in the synthesis of different classes of organic compounds have been discussed.
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Pasto DJ (1979) J Am Chem Soc 101:37; Brady WT, Roe R, Jr (1971). J Am Chem Soc 93:1662
DoMinh T, Strausz OP (1970) J Am Chem Soc 92:1766
Rey M, Roberts SM, Dreiding AS, Roussel A, Vanlierde H, Toppet S, Ghosez l (1982) Helv Chim Acta 65:703; Wasserman HH, Piper JU, Dehmlow EV (1973) J Org Chem 38:1451
Rey M, Roberts S, Dieffenbacher A (1970) Helv Chim Acta 53:417
Fleming I (2002) Pericyclic reactions. Oxford University Press, New York
Corey EJ, Desai MC (1985) Tetrahedron Lett 26:3535; Metzger C, Borrmann D, Wegler R (1967) Chem Ber 100:1817
Masamune S, Fukumoto K (1965) Tetrahedron Lett 4647
Williams JK, Wiley DW, Mckusick BC (1962) J Am Chem Soc 84:2210
Palomo C, Aizpurua JM, Ganboa I, Oiarbide M (1999) Eur J Org Chem 3223
Farina V, Hauck SI, Walker DG (1992) Synlett 761
Yamasaki H, Cvetanovic RJ (1969) J Am Chem Soc 91:520
Chapman OL, Adams WR (1968) J Am Chem Soc 99:2333
Dauben WG, Cargill RL (1961) Tetrahedron 15:197
Norman ROC, Coxon JM (1993) Principles of organic synthesis. Chapman & Hall, Oxford
Srinivasan P (1971) Org Photochem Synth 1:101
Oppolzer W (1982) Acc Chem Res 15:135; Winkler JD, McLaughlin EC (2005) Org Lett 7:227
Unett DJ, Caldwell RA, Hrncir DC (1996) J Am Chem Soc 118:1682
Corey EJ, Bass JD, Le Mahieu R, Mitra RB (1964) J Am Chem Soc 86:5570; de Mayo P (1971) Acc Chem Res 4:41
Diels O, Alder K (1928) Justus Liebigs Ann Chem 460:98
Cope C, Herrichy EC (1963) Org Syn IV:890
Wasserman A (1935) J Chem Soc 1511
Sustmann R (1974) Pure Appl Chem 40:569; (1971) Tetrahedron Lett 2717
Berson JA, Hamlet Z, Mueller WA (1962) J Am Chem Soc 84:297
Bodwell GJ, Pi Z (1997) Tetrahedron Lett 38:309
Sauer J (1967) Angew Chem Int Ed Engl 6:16
De Graw JI, Goodman L, Baker BR (1961) J Org Chem 26:1156
Spino C, Crawford J, Cui Y, Gugelchuk M (1998) J Chem Soc. Perkin Trans 2:1499
Inukai T, Kojima T (1971) J Org Chem 36:924
Inukai T, Kojima T (1966) J Org Chem 31:1121
Houk KN (1975) Acc Chem Res 8:361; (1979) Topics Current Chem 79:1; Sustmann R, Schubert R (1972) Angew Chem Int Ed Engl 11:840
Longuet-Higgins HC, Abrahamson EW (1965) J Am Chem Soc 87:2045
Zimmerman HE (1971) Acc Chem Res 4:272
Stephenson lM, Smith DE, Current SP (1982) J Org Chem 47:4170
Craig D, Shipman JJ, Fowler RB (1961) J Am Chem Soc 83:2885
Backer HJ (1939) Rec Trav Chim Pays-Bas 58:643
Stewart CA Jr (1963) J Org Chem 28:3320
Domingo LR, Jose Aurell M, Perez P, Contreras R (2002) Tetrahedron 58:4417
Rucker C, Lang D, Sauer J, Friege H, Sustmann R (1980) Chem Ber 113:1663
Paquette LA (1964) J Org Chem 29:3447
Ionescu D, Silverton JV, Dickinson LC, Miller B (1996) Tetrahedron Lett 37:1559
Wittig G (1962) Angew Chem Int Ed 1:415
Dewar MJS, de Llano D (1969) 91;789
Ciganek E (1967) Tetrahedron Lett 3321
Hamer J, Ahmad M (1967) In: Hamer J (ed) 1,4-cycloaddition reactions. Academic Press, New York
Domingo LR, Andres J, Alves CN (2002) Eur J Org Chem 2557
Atterton JCC, Jones S (2003) Tetrahedron 59:9039
Woodward RB, Sondheimer F, Taub D, Heusler K, Mc Lamore WM (1952) J Am Chem Soc 74:4223
Ranganathan S, Ranganathan D, Mehrotra AK (1974) J Am Chem Soc 96:5261
Corey EJ, Weinshenker NM, Schaaf TK, Huber W (1969) J Am Chem Soc 91:5675
Bartlett PA, Green FR, Webb TR (1977) Tetrahedron Lett 331; Ranganathan D, Rao CB, Ranganathan S, Mehrotra AK, Iyengar R (1980) J Org Chem 45:1185
Ronan B, Kagan HB (1992) Tetrahedron Asymm 3:115
Paquette LA, Moerck RE, Harirchian B, Magnus PD (1978) J Am Chem Soc 100:1597
Davis AP, Whitham GH (1980) J Chem Soc Chem Commun 639
Girard C, Bloch R (1982) Tetrahedron Lett 23:3683
Carruthers W (1993) Some modern methods of organic synthesis. Cambridge University Press, New Delhi
Ciganek E (1967) Tetrahedron Lett 3321
Fringuelli F, Tatiedri A (1990) Dienes in diels alder reactions. Wiley, New York; Alston PV, Ottenbrite RM, Newby J (1979) J Org Chem 44:4939
Deem ML (1972) Synthesis 675; Oppolzer W, Chapuis C (1983) Tetrahedron Lett 24:4665
Trost BM, Bridges AJ (1976) J Am Chem Soc 98:5017
Oppolzer W (1977) Angew Chem Int Ed Engl 16:10
Arnold BJ, Sammes PG, Wallace TW (1974) J Chem Soc Perkin Trans 1(409):415
Mann J, Piper SE (1982) J Chem Soc, Chem Commun 430
Wittig G, Burger TF (1966) 0). Justus Liebigs Ann Chem 632:85
Ono N, Miyaki H, Kaji A (1982) Chem Commun 33
Singh J (2009) Photochemistry and pericyclic reactions 3rd edn. New Academic Science
Ireland RE, Daub JP (1983) J Org Chem 48:1303
Danishefsky S, Kitahara T (1974) J Am Chem Soc 96:7807
Danishefsky S, Singh RK, Gammill RB (1978) J Org Chem 43:379
Ross AG, Townshed SD, Danishefsky S (2013) J Org Chem 78:204
Serckx Poncin B, Hesbain- Prizque AM, Ghosez L (1982) Tetrahedron Lett 23:3261
Demoulin A, Gorissen H, Hesbain- Frisque AM, Ghosez L (1975) J Am Chem Soc 97:4409
Harris EE, Firestone RA, Pfister K, Boettcher RR, Cross FJ, Currie R (1962) J Org Chem 27:2705
Hamer J, Ahmad M (1967) In: Harmer J (ed) 1,4 Cycloaddition reactions. Academic Press, New York; Mc Clure KM, Danishefsky SJ (1991) J Org Chem 56:850
Weinreb SM, Staib RR (1982) Tetrahedron 39:3087
Gillis BT (1967) In: Hamer J (ed) 1,4 cycloaddition reactions. Academic Press, New York
Jurczak J, Zamojski A (1972) Tetrahedron 28:1505
Hoffmann HMR, Joy DR, Suter AK (1968) J Chem Soc B 57; Hoffmann HMR, Joy DR (1968) J Chem Soc B 1182
Shimizu N, Tanaka M, Tsuno Y (1982) J Am Chem Soc 104:1330
Turro NJ, Adelson SS, Williams JR, Darling TR, Hammond WB (1969) J Am Chem Soc 91:2283; Elderson SS, Turro NJ (1970) J Am Chem Soc 92:2770; Chan CH, Li MP, Mychajlowskij W, Harp DN (1974) Tetrahedron Lett 35
Kauffmann T (1974) Angew Chem Int Ed 13:627
Kagan HB, Riant O (1992) Chem Rev 92:1007; Oppolzer W (1984) Angew Chem Int Ed Engl 23:876
Poll T, Helmchen G, Bauer B (1984) Tetrahedron Lett 2191
Avenoza A, Cativiela C, Mayoral JA, Peregrina JM (1992) Tetrahedron Asymmetry 3:913; Cativiela C, Mayoral JA, Avenoza A, Peregrina JM, Lahoz FJ, Gimeno S (1992) J Org Chem 57:4664
Corey EJ, Loh TP (1991) J Am Chem Soc 113:8966
Yao S, Johannsen M, Audrain H, Hazell RG, Jorgensen KA (1998) J Am Chem Soc 120:8599
Mikami K, Motoyama Y, Terada M (1994) J Am Chem Soc 116:2812
Kobayashi S (1998) Pure Appl Chem 70:1019
Zhang X, Du H, Wang Z, Wu YD, Ding K (2006) J Org Chem 71:2862
Pegot B, Buu ONV, Gori D, Vo-Thanh G (2006) Beilstein J Org Chem 2:18
Taber DF, Gunn BP (1979) J Am Chem Soc 101:3992; Kitahara T, Kurata H, Matsuoka T, Mori K (1985) Tetrahedron 41:5475
Wilson SR, Mao DT (1978) J Am Chem Soc 100:6289
Yuki K, Shindo M, Shishido K (2001) Tetrahedron Lett 42:2517
Roush WR, Gillis HR, Ko AI (1982) J Am Chem Soc 104:2269
Shea KJ, Wise S, Burke LD, Davis PD, Gilman JW, Greeley AC (1982) J Am Chem Soc 104:5708
Shea KJ, Gilman JW (1983) Tetrahedron Lett 24:657
Roush WR, Gillis HR (1982) J Org Chem 47:4825
Gricco PA, Takigawa T, Schilling WJ (1980) J Org Chem 45:2247
Yeh MCP, Tsao WC, Liu CJ (2005) J Chin Chem Soc 52:2247; Harmata M (2001) Acc Chem Res 34:595
Gaitzsch J, Rogachev VO, Metz P, Yusubov MS, Filimonov VD, Kataeva O (2009) J Sulfur Chem 30:4
Alder K, Muders R, Krane W, Wirtz P (1959) Ann 627:58
Starck F, Jones PG, Herges R (1998) Eur J Org Chem 2533
Boger DL, Duff SR, Panck JS, Yasuda M (1985) J Org Chem 50:5782
Jones M Jr, Reich SD, Scott LT (1970) J Am Chem Soc 92:3118
Kadaba PK (1969) Tetrahedron 25:3053; Huisgen R, Szeimies G, Mobius L (1967) Chem Ber 100:2494
Bihlmaier W, Geittner J, Huisgen R, Reissig HU (1978) Heterocycles 10:147
Huisgen R, Eberhard P (1971) Tetrahedron Lett 4343
Sustmann R, Trill H (1972) Angew Chem Int Ed Engl 11:838
Houk KN, Sims J, Duke BE, Jr, Strozier RW, George JK (1973) J Am Chem Soc 95:7287; Sims J, Houk KN (1973) J Am Chem Soc 95:5798
Huisgen R, Szeimies G, Mobius L (1967) Chem Ber 100:2494
Kanemasa S, Ueno N, Shirahase M (2002) Tetrahedron Lett 43:657
Jensen KB, Gothelf KV, Hazell RG, Jorgensen KA (1997) J Org Chem 62:2471
Chiacchio U, Casuscelli F, Corsaro A, Rescifina A, Romeo G, Uccella N (1994) Tetrahedron 50:6671
Simonsen KB, Bayon P, Hazel RG, Gothelf KV, Jorgensen KA (1999) J Am Chem Soc 121, 3845
Kozikowski AP, Ghosh AK (1982) J Am Chem Soc 104:5788
Huisen R, Hauck H, Grashey R, Seidl H (1968) Chem Ber 101:2568
Huisgen R, Szeimies G (1965) Chem Ber 98:1153
Scheiner P, Schomaker JH, Deming S, Libbey WJ, Nowack GP (1965) J Am Chem Soc 87:306
Curran DP (1982) J Am Chem Soc 104:4024
Huisgen R (1963) Angew Chem Int Ed 2:633
Padwa A (1983) 1,3-dipolar cycloaddition chemistry, general heterocyclic chemistry series 1. Wiley, New York, pp 141–145
Huisgen R, Scheer W, Szeimies G, Huber H (1966) Tetrahedron Lett 397
Ugarriza I, Uria U, Reyes E, Carillo L, Vicario JL (2015) Asymmetric Catal 2:7
Huisgen R, Hauck H, Grashey R, Scidl H (1968) Chem Ber 101:2568
Joucla M (1973) Tetrahedron 29:2315
Winterfeldt E, Krohn W, Stracke H (1969) Chem Ber 102:2346
Huisgen R (1977) Angew Chem Int Ed Engl 16:572
Toyoda J, Ibata T, Tamura H, Ogawa K, Nishino T, Takebayashi M (1985) Bull Chem Soc Jpn 58: 2212; Ibata T, Toyada J, Sawada M, Tanaka T (1986) J Chem Soc, Chem Commun 1266
Tufariello JJ, Mullen GB, Tegeler JJ, Trybulski EJ, Wong SC, Ali SA (1979) J Am Chem Soc 101:2435
Tufariello JJ (1979) Acc Chem Res 12:396
Le Bel NA, Hwang D (1978) Org Synth 58:106
LeBel NA, Balasubramanian N (1989) J Am Chem Soc 111:3363
Roussi G (1990) Heterocycles 31:1445
Seitz G, Tegethoff R (1993) Arch Pharm 326:135
Novikov MS, Khlebnikov AF, Besedina OV, Kostikov RR (2001) Tetrahedron Lett 42:533
Engel E, Steglich W (1978) Angew Chem 90:719; ibid(1978) Angew Chem Int Ed Engl 17:676
Kozikowski AP, Stein PD (1982) J Am Chem Soc 104:4023
Confalone PN, Lollar ED, Pizzolato G (1978) J Am Chem Soc 100:6291
Kanemasa S (2002) Synlett 1371
Holland JM, Jones DW (1969) Chem Commun 587
Mukai T, Tezuka T, Akasaki Y (1966) J Am Chem Soc 88:5025
Mukherjee D, Watts CR, Houk KN (1978) J Org Chem 43:817
Houk KN, Woodward RB (1970) J Am Chem Soc 92:4145
Ban T, Wakita Y, Kanematsu K (1980) J Am Chem Soc 102:5416
Funk RL, Bolton GL (1986) J Am Chem Soc 108:4655
Paquette LA, Barrett JH (1966) J Am Chem Soc 88:2590
Rigby JW, Ateeq HS, Charles NR, Cuisiat SV, Ferguson MD (1993) J Am Chem Soc 115:1382
Doering WVE, Wiley DW (1960) Tetrahedron 11:183
Galbraith A, Small T, Barnes RA, Boekelheide V (1961) J Am Chem Soc 83:453
Bindl J, Burgemeister T, Daub J (1985) Justus Liebigs Ann Chem 1346
Le Goff E (1962) J Am Chem Soc 84:3975
Liu CY, Houk KN (1987) Tetrahedron Lett 28:1367
Pham W, Weissleder R, Tung CH (2002) Tetrahedron Lett 43:19
Prinzbach H, Knoefel H (1969) Angew Chem Int Ed Engl 8:881
Woodward RB, Hoffmann R (1971) The conservation of orbital symmetry. Academic Press, New York, p 85
Lemal DM, Mc Gregor SD (1966) J Am Chem Soc 88:1335
Mock WL (1966) J Am Chem Soc 88:2857; Mc Gregor SD, Lemal DM (1966) J Am Chem Soc 88:2858
Ogliaruso MA, Romanelli MG, Becker EI (1965) Chem Rev 65:261
Allen CFH, Van Allen JA (1950) J Am Chem Soc 72:5165
Mc Intosh JM, Sieler RA (1978) J Org Chem 43:4431
Cava MP, Mitchell MJ, Deana AA (1960) J Org Chem 25:1481
Nicolaou KC, Barnette WE, Ma P (1980) J Org Chem 45:1463
Cava MP (1959) J Am Chem Soc 81:4266
Isaac NS, Laila AAR (1976) Tetrahedron Lett 17:715
Souto JA, Lopez CS, Faza ON, Alvarez R, de Lera AR (2005) Org Lett 7:1565
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Dinda, B. (2017). Cycloaddition Reactions. 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_3
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