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DOI: 10.1055/s-2001-15076
Intramolecular [2+2] Photocycloaddition of Bichromophoric Derivatives of 3,5-Dihydroxybenzoic Acid and 3,5-Dihydroxybenzonitrile
Publication History
Publication Date:
24 September 2004 (online)
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Abstract
The irradiation of 3-alkenyloxy-5-hydroxybenzoic acid derivatives 1a-d yields highly functionalized alkyloxyenone derivatives when the reaction is carried out in the presence of acid. A higher reactivity is observed for the corresponding 3-alkenyloxy-5-hydroxybenzonitrile compounds 7a, b, which also react in neutral reaction media. In the first step of the reaction, a [2+2] photocycloaddition occurs. The following steps, leading to stable final products, need acid catalysis in the case of the substrates 1a-d. The irradiation of the benzonitrile derivative 7b also furnishes the side product 9, which results from a [2+3] photocycloaddition.
Key words
photochemistry - cycloaddition - arenes - acidic reaction medium - herbicides
-
1a
Bryce-Smith D.Gilbert A.Orger B.Tyrrell H. J. Chem. Soc., Chem. Commun. 1974, 334 -
1b
Leismann H.Mattay J.Scharf HD. J. Am. Chem. Soc. 1984, 106: 3985 -
1c
Mattay J.Runsink J.Gersdorf J.Rumbach T.Ly C. Helv. Chim. Acta 1986, 69: 442 -
1d
Müller F.Mattay J. Chem. Rev. 1993, 93: 99 -
2a
Barentsen HM.Talman EG.Piet DP.Cornelisse J. Tetrahedron 1995, 51: 7469 -
2b
Barentsen HM.Sieval AB.Cornelisse J. Tetrahedron 1995, 51: 7495 -
2c
Van der Eycken E.De Keukeleire D.De Bruyn A.Van der Eycken J.Gilbert A. Recl. Trav. Chim. Pays-Bas 1995, 114: 480 -
2d
Blakemore DC.Gilbert A. Tetrahedron Lett. 1994, 35: 5267 -
2e
Blakemore DC.Gilbert A. Tetrahedron Lett. 1995, 36: 2307 -
2f
Amey DM.Gilbert A.Jones DT. J. Chem. Soc., Perkin Trans. 2 1998, 213 -
2g
Weber G.Runsink J.Mattay J. J. Chem. Soc., Perkin Trans. 1 1987, 2333 -
2h
Mattay J.Rumbach T.Runsink J. J. Org. Chem. 1990, 55: 5691 -
2i
Cornelisse J. Chem. Rev. 1993, 93: 615 -
2j
Wender PA.Dore TM.de Long MA. Tetrahedron Lett. 1996, 37: 7687 -
2k
Wender PA.Dore TM. Tetrahedron Lett. 1998, 39: 8589 -
2l
Zhang C.Bourgin D.Keese R. Tetrahedron 1991, 47: 3059 -
2m
Baralotto C.Chanon M.Julliard M. J. Org. Chem. 1996, 61: 3576 -
2n
Avent AG.Bryne PW.Penkett CS. Org. Lett. 1999, 1: 2073 -
2o
Wender PA.Ternansky R.de Long M.Singh S.Olivero A.Rice K. Pure Appl. Chem. 1990, 62: 1597 -
2p
Wender PA.Siggel L.Nuss JM. Comprehensive Organic Synthesis Vol. 5:Trost BM.Fleming I.Paquette LA. Pergamon Press; Oxford: 1991. p.645-673 -
2q
Wender PA.Siggel L.Nuss JM. Organic Photochemistry Vol. 10:Padwa A. Marcel Dekker; New York: 1989. p.357-473 -
2r
Wender PA.Dore TM. CRC Handbook of Photochemistry and PhotobiologyHorspool WM.Song P.-S. CRC Press; Boca Raton: 1995. p.280-290 -
3a
Vízvárdi K.Toppet S.Hoonaert GJ.De Keukeleire D.Bakó P.Van der Eycken E. J. Photochem. Photobiol., A 2000, 133: 135 -
3b
Van der Eycken E.De Keukeleire D.De Bruyn A. Tetrahedron Lett. 1995, 36: 3573 -
3c
De Keukeleire D. Aldrichimica Acta 1994, 27: 59 -
3d
De Keukeleire D.He S.-L.Blakemore D.Gilbert A. J. Photochem. Photobiol., A 1994, 80: 233 -
3e
Gilbert A.Taylor GN.bin Samsudin MW. J. Chem. Soc., Perkin Trans. 1 1980, 869 -
3f
Mattay J.Leismann H.Scharf HD. Chem. Ber. 1979, 112: 577 -
3g
Kishikawa K.Akimoto S.Kohmoto S.Yamamoto M.Yamada K. J. Chem. Soc., Perkin Trans. 1 1997, 77 -
3h
Mani J.Schüttel S.Zhang C.Bigler P.Müller C.Keese R. Helv. Chim. Acta 1989, 72: 487 -
3i
De Keukeleire D.He S.-L. Chem. Rev. 1993, 93: 359 -
4a
Bryce-Smith D.Gilbert A. Tetrahedron 1976, 32: 1309 -
4b
Bryce-Smith D.Gilbert A. Tetrahedron 1977, 33: 2459 -
4c
Houk KN. Pure Appl. Chem. 1982, 54: 1633 -
4d
van der Hart JA.Mulder JJC.Cornelisse J. J. Mol. Struct. (Theochem) 1987, 151: 1 -
4e
van der Hart JA.Mulder JJC.Cornelisse J. J. Photochem. Photobiol., A 1991, 61: 3 -
4f
Stehouwer AM.van der Hart JA.Mulder JJC.Cornelisse J. J. Mol. Struct. (Theochem.) 1992, 92: 333 -
4g
van der Hart JA.Mulder JJC.Cornelisse J. J. Photochem. Photobiol., A 1995, 86: 141 - 5
Clifford S.Bearpark MJ.Bernardi F.Olivucci M.Robb MA.Smith BR. J. Am. Chem. Soc. 1996, 118: 7353 -
6a
Wagner PJ.McMahon K. J. Am. Chem. Soc. 1994, 116: 10827 -
6b
Wagner PJ.Cheng K.-L. Tetrahedron Lett. 1993, 34: 907 -
6c
Smart RP.Wagner PJ. Tetrahedron Lett. 1995, 36: 5131 -
6d
Wagner PJ.Smart RP. Tetrahedron Lett. 1995, 36: 5135 -
6e
Nuss JM.Chinn JP.Murphy MM. J. Am. Chem. Soc. 1995, 117: 6801 -
6f
Busson R.Schraml J.Saeyens W.Van der Eycken E.Herdewijn P.De Keukeleire D. Bull. Soc. Chim. Belg. 1997, 106: 671 -
6g
de Haan R. Proefschrift Rijksuniversiteit te Leiden; Netherlands: 1996. -
6h
Al-Qaradawi S.Gilbert A.Jones DT. Recl. Trav. Chim. Pays-Bas 1995, 114: 485 -
6i
Cosstick KB.Drew MGB.Gilbert A. J. Chem. Soc., Chem. Commun. 1987, 1867 -
6j
Al-Qaradawi SY.Cosstick KB.Gilbert A. J. Chem. Soc., Perkin Trans. 1 1992, 1145 -
7a
McCullough JJ. Chem. Rev. 1987, 87: 811 -
7b
Döpp D.Memarian HR. Chem. Ber. 1990, 123: 315 -
7c
Döpp D.Erian AW.Henkel G. Chem. Ber. 1993, 126: 239 -
7d
Lanfermann H.Döpp D. J. Inform. Rec. Mats. 1994, 21: 545 -
7e
Memarian HR.Nasr-Esfahani M.Boese R.Döpp D. Liebigs Ann./Receuil 1997, 1023 -
7f
Al-Jalal NA. J. Chem. Res., Synop. 1995, 44 -
7g
Al-Jalal NA.Prichard RG.McAuliffe CA. J. Chem. Res. Synop. 1994, 452 -
7h
Mizuno K.Konishi S.Yoshimi Y.Sugimoto A. Chem. Commun. 1998, 1659 -
7i
Wagner PJ.Sakamoto M. J. Am. Chem. Soc. 1989, 111: 9254 -
7j
Noh T.Kim D.Kim Y.-J. J. Org. Chem. 1998, 63: 1212 -
8a
Hoffmann N.Pete JP. Tetrahedron Lett. 1996, 37: 2027 -
8b
Hoffmann N.Pete JP. J. Org. Chem. 1997, 62: 6952 -
8c
Hoffmann N.Pete JP. J. Inform. Record. 1998, 24: 133 -
8d
Verrat C.Hoffmann N.Pete JP. Synlett 2000, 1166 - For the influence of acidic media in similar reactions see:
-
9a
Kalena GP.Pradhan P.Banerji A. Tetrahedron Lett. 1992, 55: 7775 -
9b
Kalena GP.Pradhan P.Banerji A. Tetrahedron 1999, 55: 3209 -
9c
Ohkura K.Kanazashi N.Seki K. Chem. Pharm. Bull. 1993, 41: 239 -
9d
Ohkura K.Seki K.Hiramatsu H.Aoe K.Terashima M. Heterocycles 1997, 44: 467 -
9e
Ohkura K.Noguchi Y.Seki K. Heterocycles 1998, 47: 429 -
9f
Howell N.Pincock JA.Stefanova R. J. Org. Chem. 2000, 65: 6173 -
9g
Matohara K.Lim C.Yasutake M.Nogita R.Koga T.Sakamoto Y.Shinmyozu T. Tetrahedron Lett. 2000, 41: 6803 -
9h
Mori T.Wada T.Inoue Y. Org. Lett. 2000, 2: 3401 - 10
Hoffmann N.Pete JP. Tetrahedron Lett. 1995, 36: 2623 - 11
Hoffmann N.Pete JP. Tetrahedron Lett. 1998, 39: 5027 - 13
Kavarnos GJ. Fundamentals of Photoinduced Electron Transfer VCH; New York: 1993. -
14a
Kubo Y.Kusumoto K.Nakajima S.Inamura I. Chem. Lett. 1999, 113 -
14b
Kubo Y.Adachi T.Miyahara N.Nakajima S.Inamura I. Tetrahedron Lett. 1998, 39: 9477 -
14c
Kubo Y.Yoshioka M.Kiuchi K.Nakajima S.Inamura I. Tetrahedron Lett. 1999, 40: 527 -
14d
Kubo Y.Inoue T.Sakai H. J. Am. Chem. Soc. 1992, 114: 7660 -
14e
Saito I.Shimozono K.Matsuura T. J. Am. Chem. Soc. 1983, 105: 963 -
14f
Andersen S.Margaretha P. J. Photochem. Photobiol., A 1998, 112: 135 -
14g
Schwebel D.Ziegenbalg J.Kopf J.Margaretha P. Helv. Chim. Acta 1999, 82: 177 -
15a
Maier A.Golz A.Lichtenthaler HK.Meyer N.Retzlaff G. Pestic. Sci. 1994, 42: 153 -
15b
Liepa AJ.Wilkie JS.Winkler DA.Winzenberg KA. Aust. J. Chem. 1992, 45: 759 -
15c
Burton JD.Gronwald JW.Somers DA.Connelly JA.Gengenbach BG.Wyse DL. Biochem. Biophys. Res. Commun. 1987, 148: 1039 -
15d
Rendina AR.Felts JM. Plant Physiol. 1988, 86: 983 -
16a
Imai H.Uemori Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793 -
16b
Crombie L.Jamieson SV. J. Chem. Soc., Perkin Trans. 1 1982, 1467 -
16c
Gibson HW.Nagvekar DS. Can. J. Chem. 1997, 75: 1375 - 17
Wagner G. Arch. Pharm. (Weinheim, Ger.) 1959, 292: 282 - 18
McOmie JFW.Watts ML.West DE. Tetrahedron 1968, 24: 2289 - 19
Halton DD.Morrison GA. J. Chem. Res., Miniprint 1979, 301 - 20
Chakraborty TK.Reddy GV. J. Org. Chem. 1992, 57: 5462
References and Notes
When 7b was irradiated at λ = 300 nm in acetone, a decrease of the conversion rate and the amount of 8b was observed. No formation of compound 9 could be detected. In contrast, when the reaction of 7a was carried out in the presence of 1,3-cyclohexadiene (1.5 m/L, ET = 52.4 kcal/mol; (Murov, S. L. Handbook of Photochemistry; Marcel Dekker: New York, 1973) in acetonitrile-toluene (1:1), the formation of 8a was not affected. These results led us to conclude that the formation of the products 8a and 8b results from a transformation of 7a or 7b in their singlet excited state.