RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2017; 49(03): 539-553
DOI: 10.1055/s-0036-1588645
DOI: 10.1055/s-0036-1588645
feature
Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release
Weitere Informationen
Publikationsverlauf
Received: 13. Oktober 2016
Accepted after revision: 13. Oktober 2016
Publikationsdatum:
01. Dezember 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201703/lookinside/thumbnails/ss-2016-e0569-fa_10-1055_s-0036-1588645-1.jpg)
Abstract
Five families of caged fragrance compounds that allow the storage and release of the following small volatile organic molecules are described: terpene hydrocarbons, aldehydes, ketones, Michael-type α,β-unsaturated enones, and carboxylic acids and esters. These caged molecules are released by photoexcitation via carbonyl-directed hydrogen-transfer processes and subsequent C–C bond cleavage (Norrish Type II) or by didenitrogenation of diazirines.
Key words
caged molecules - photochemistry - hydrogen transfer - carbonyl compounds - dinitrogen releaseSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588645.
- Supporting Information
-
References
- 1 Goeldner M, Givens R. Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules. Wiley-VCH; Weinheim: 2005
- 2 Lemke EA, Summerer D, Geierstanger BH, Brittain SM, Schultz PG. Nat. Chem. Biol. 2007; 3: 769
- 3 Gonzales MA, Mascharak PK. J. Inorg. Biochem. 2014; 133: 127
- 4 Cram DJ, Tanner ME, Thomas R. Angew. Chem., Int. Ed. Engl. 1991; 30: 1024
- 5 Smith E, Collins I. Future Med. Chem. 2015; 7: 159
- 6 Xia Y, Peng L. Chem. Rev. 2013; 113: 7880
- 7 Chaulk SG, MacMillan AM. Nat. Protoc. 2007; 2: 1052
- 8 Pelliccioli A, Wirz J. Photochem. Photobiol. Sci. 2002; 1: 441
- 9 Falvey DE, Sundararajan C. Photochem. Photobiol. Sci. 2004; 3: 831
- 10a Idris NM, Gnanasammandhan I, Bansal A, Zhang Y. Chem. Soc. Rev. 2015; 44: 1449
- 10b Sortino S. J. Mater. Chem. 2012; 22: 301
- 10c Shao Q, Xing B. Chem. Soc. Rev. 2010; 39: 2835
- 10d Blake JA, Bareiss B, Jimenez L, Griffith M, Scaiano JC. Photochem. Photobiol. Sci. 2012; 11: 539
- 11 Alvarez-Lorenzo C, Bromberg L, Concheiro A. Photochem. Photobiol. 2009; 85: 848
- 12a Sanghamitra A, Ikbal M, Kumar A, Singh ND. P. J. Photochem. Photobiol., B 2012; 111: 39
- 12b Liu X, Macaulay ED. M, Pickett JA. J. Chem. Ecol. 1984; 10: 809
- 13 Bochet CG, Blanc A In Handbook of Photochemistry. Vol. 1. Griesbeck A, Oelgemöller M, Ghetti F. CRC Press; Boca Raton: 2012: 73
- 14 Klan P, Solomek T, Bochet C, Blanc A, Givens R, Rubina M, Popik V, Kostikov A, Wirz J. Chem. Rev. 2013; 113: 119
- 15 Solomek T, Wirz J, Klan P. Acc. Chem. Res. 2015; 48: 3064
- 16 Luchowski R, Matveeva EG, Shtoyko T, Sarkar P, Patsenker LD, Klochko OP, Terpetschnig EA, Borejdo J, Akopova I, Gryczynski Z, Gryczynski I. Curr. Pharm. Biotechnol. 2010; 11: 96
- 17 Pandurangi RS, Karra SR, Kuntz RR, Volkert WA. Photochem. Photobiol. 1996; 64: 100
- 18 Ford PC, Wecksler S. Coord. Chem. Rev. 2005; 249: 1382
- 19 Vittorino E, Cicciarella E, Sortino S. Chem. Eur. J. 2009; 15: 6802
- 20 Givens RS, Rubina M, Wirz J. Photochem. Photobiol. Sci. 2012; 11: 472
- 21 Ohtsuki T, Miki S, Kobayashi S, Haraguchi T, Nakata E, Hirakawa K, Sumita K, Watanabe K, Okazaki S. Sci. Rep. 2015; 5: No. 18577
- 22 Levrand B, Herrmann A. Chimia 2007; 61: 661
- 23a Herrmann A. Photochem. Photobiol. Sci. 2012; 11: 446
- 23b Herrmann A. Angew. Chem. Int. Ed. 2007; 46: 5836
- 23c Levrand B, Fieber W, Lehn JM, Herrmann A. Helv. Chim. Acta 2007; 90: 2281
- 23d Gautschi M, Bajgrowicz JA, Kraft P. Chimia 2001; 55: 379
- 23e Derrer S, Flachsmann F, Plessis C, Stang M. Chimia 2007; 61: 665
- 25 Wagner PJ In Handbook of Photochemistry. Horspool WH, Song P.-S. CRC Press; Boca Raton: 1994: 449
- 26 Norrish RG. W, Appleyard ME. S. J. Chem. Soc. 1934; 874
- 27 McMillan GR, Calvert JG, Pitts JN. Jr. J. Am. Chem. Soc. 1964; 86: 3602
- 28 Yang NC, Yang D.-H. J. Am. Chem. Soc. 1958; 80: 2913
- 29 Small RD. Jr, Scaiano JC. Chem. Phys. Lett. 1977; 50: 431
- 30 Johnston LJ, Scaiano JC. Chem. Rev. 1989; 89: 521
- 31 Cai X, Cygon P, Goldfuss B, Griesbeck AG, Heckroth H, Fujitsuka M, Majima T. Chem. Eur. J. 2006; 12: 4662
- 32 Srikrishna A, Vijaykumar D, Reddy TJ. Tetrahedron 1997; 53: 1439
- 33 Ouellet SG, Tuttle JB, MacMillan DW. C. J. Am. Chem. Soc. 2005; 127: 32
- 34 Pietrzak M, Jedrzejewska B. J. Organomet. Chem. 2011; 696: 2135
- 35 Muzart J, Ajjou AN. Synthesis 1993; 785
- 36 Brown HC, Zweifel G. J. Am. Chem. Soc. 1961; 83: 1241
- 37 Carman RM, Garner AC. Aust. J. Chem. 1995; 48: 1301
- 38 Williams DR, Phillips JG. J. Org. Chem. 1981; 46: 5452
- 39 Yamashita M, Matsumiya K, Morimoto H, Suemitsu R. Bull. Chem. Soc. Jpn. 1989; 62: 1668
- 40 Griesbeck AG, Hinze O, Görner H, Huchel U, Kropf C, Sundermeier U, Gerke T. Photochem. Photobiol. Sci. 2012; 11: 587
- 41 Xu M, Lukeman M, Wan P. J. Photochem. Photobiol., A 2009; 204: 52
- 42 Kuhn HJ, Braslavsky SE, Schmidt R. Pure Appl. Chem. 2004; 76: 2105
- 43 Zepp RG, Gumz MM, Miller WL, Gao H. J. Phys. Chem. A 1998; 102: 5716
- 44 Mukaiyama T, Stevens RW, Iwasawa N. Chem. Lett. 1982; 353
- 45 Mukaiyama T, Iwasaw N, Stevens RW, Haga T. Tetrahedron 1984; 40: 1381
- 46 Serra S. Molecules 2015; 20: 12817
- 47 Imamoto T, Kusumoto T, Yokoyama M. Tetrahedron Lett. 1983; 24: 5233
- 48 Christoffers J. J. Chem. Soc., Perkin Trans. 1 1997; 3141
- 49 Alonso-Gomez JL, Pazos Y, Navarro-Vazquez A, Lugtenburg J, Cid MM. Org. Lett. 2005; 7: 3773
- 50 Wahl B, Philipson Y, Bonin H, Mortreux A, Sauthier M. J. Org. Chem. 2013; 78: 1547
- 51 Iglesias E. J. Chem. Soc., Perkin Trans. 2 1997; 431
- 52 Hu X, Zhang Q, Yu H, Zhao D, Dong S, Zhou W, Tang Z. J. Appl. Spectrosc. 2015; 81: 949
- 53 Murphy SW. S. J. Chem. Soc., Perkin Trans. 1 1986; 1445
- 54 Wessig P, Mühling O In Molecular and Supramolecular Photochemistry. Vol. 12. Griesbeck AG, Mattay J. Dekker; New York: 2005: 41
- 55 Wagner G, Knoll W, Bobek MM, Brecker L, Van Herwijnen HW. G, Brinker UH. Org. Lett. 2010; 12: 332
- 56 Knoll W, Kaneno D, Bobek MM, Brecker L, Rosenberg MG, Tomoda S, Brinker UH. J. Org. Chem. 2012; 77: 1340
- 57 Shustov GV, Varlamov SV, Rauk A, Kostyanovskii RG. J. Am. Chem. Soc. 1990; 112: 3403
- 58 Modarelli DA, Morgan S, Platz MS. J. Am. Chem. Soc. 1992; 114: 7034
- 59 Rosenberg MG, Kam SM, Brinker UH. Tetrahedron Lett. 1996; 37: 3235
- 60 Griesbeck, A. G.; Landes, A.; Huchel, U.; Kropf, C.; Gerke, T. unpublished results.
- 61 Matsumoto S, Koitabashi S, Otani Y, Akazome M. Tetrahedron Lett. 2015; 56: 4320
- 62 Villa G, Povie G, Renaud P. J. Am. Chem. Soc. 2011; 133: 5913