Gas-phase synthesis of hydrodiphenylcyclopropenylium via nonclassical favorskii rearrangement from alkalicationized α,α′-dibromodibenzyl ketone

Rapid Communications in Mass Spectrometry

Volumn 24, Issue 17, 2010, Pages 2665-2672

  Zhao, Zhi Xiong ^a   Wang, Hao Yang ^a   Xu, Chu ^a   Guo, Yin Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSPRAY IONIZATION; GASES; IONIZATION OF GASES; MASS SPECTROMETRY;

ALKALI METAL CATIONIZATION; CATIONIZED; DEBROMINATION; DIPHENYLCYCLOPROPENONE; ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; ESI-MS-MS; GAS-PHASE SYNTHESIS; LEWIS ACID; PROTONATED; THEORETICAL METHODS;

KETONES;

EID: 77955403181     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.4694     Document Type: Article

References (40)

1. Favorskii AE. J. Russ. Phys. Chem. Soc. 1894; 26: 559.
2. Kurti L, Czako B, Strategic Applications of Named Reactions in Organic Synthesis. Elsevier Press, 2005; 164.
3. Llera JM, Fraser-Reid B. J. Org. Chem. 1989; 54: 5544.
4. Takeshita H, Kawakami H, Ikeda Y, Mori A. J. Org. Chem. 1994; 59: 6490.
5. Loftfield RB. J. Am. Chem. Soc. 1950; 72: 632.
6. Loftfield RB. J. Am. Chem. Soc. 1951; 73: 4707.
7. Lienhard GE, Wang T-C. J. Am. Chem. Soc. 1969; 91: 1146.
8. Breslow R, Posxer J, Krebs A. J. Am. Chem. Soc. 1963; 85: 234.
9. Fenn JB, Mann M, Meng CK, Wong SF, Whitehouse CM. Mass Spectrom. Rev. 1990; 9: 37.
10. O'Hair RAJ. Chem. Commun. 2006; 1469.
11. Rijs N, Khairallah GN, Waters T, O'Hair RAJ. J. Am. Chem. Soc. 2008; 130: 1069.
12. O'Hair RAJ, Waters T, Cao B. Angew. Chem. Int. Ed. 2007; 46: 7048.
13. Khairallah GN, O'Hair RAJ. Angew. Chem. Int. Ed. 2005; 44: 728.
14. O'Hair RAJ, Vrkic AK, James PF. J. Am. Chem. Soc. 2004; 126: 12173.
15. Tian Z, Chan B, Sullivan MB, Radom L, Kass SR. Proc. Natl. Acad. Sci. USA 2008; 105: 7647.
16. Khairallah GN, O'Hair RAJ. Dalton Trans. 2008; 2956.
17. Meyer MM, Khairallah GN, Kass SR, O'Hair RAJ. Angew. Chem. Int. Ed. 2009; 48: 2934.
18. Hao-Yang Wang, Xiang Zhang, Guo Y-L, Tang Q-H, Lu L. J. Am. Soc. Mass Spectrom. 2006; 17: 253.
19. Chen H, Eberlin LS, Nefliu M, Augusti R, Cooks RG. Angew. Chem. Int. Ed. 2008; 47: 3422.
20. Wang H-Y, Yim W-L, Klüner T, Metzger JO. Chem. Eur. J. 2009; 15: 10948.
21. Krebs AW. Angew. Chem. Int. Ed. 1965; 4: 10.
22. Komatsu K, Kitagawa T. Chem. Rev. 2003; 103: 1371.
23. Hückel E. Zeitschrift für Physik A Hadrons and Nuclei. 1931; 70: 204.
24. Inagaki S, Hirabayashi Y. J. Am. Chem. Soc. 1977; 99: 7418.
25. Potts KT, Baum JS. Chem. Rev. 1974; 74: 189.
26. Roberts JD, Streitwieser A, Regan CM. J. Am. Chem. Soc. 1952; 74: 4579.
27. Bohlmann F, Jakupovic J, Müller L, Schuster A. Angew. Chem. Int. Ed. Engl. 1981; 20: 292.
28. Kogen H, Kiho T, Tago K, Miyamoto S, Fujioka T, Otsuka N, Suzuki-Konagai K, Ogita T. J. Am. Chem. Soc. 2000; 122: 1842.
29. Ando R, Morinaka Y, Tokuyama H, Isaka M, Nakamura E. J. Am. Chem. Soc. 1993; 115: 1174.
30. Hardee DJ, Kovalchuke L, Lambert TH. J. Am. Chem. Soc. 2010; 132: 5002.
31. Kelly BD, Lambert TH. J. Am. Chem. Soc. 2009; 131: 13930.
32. Vol'pin ME, Koreshkov YD, Kursanov DN. Dokl. Akad. Nauk SSSR, Ser. Khim. 1959; 3: 506.
33. Breslow R, Haynie R, Mirra J. J. Am. Chem. Soc. 1959; 81: 247.
34. Hopkins HP, Bostwick D, Alexander CJ. J. Am. Chem. Soc. 1976; 98: 1355.
35. Kuzmanich G, Gard MN, Garcia-Garibay MA. J. Am. Chem. Soc. 2009; 131: 11606.
36. Sander W, Chapman OL. Angew. Chem. Int. Ed. Engl. 1988; 27: 398.
37. Poloukhtine A, Popik VV. J. Org. Chem. 2003; 68: 7833.
38. Breslow R, Eicher T, Krebs A, Peterson RA, Posner J. J. Am. Chem. Soc. 1965; 87: 1320.
39. Becke AD. J. Chem. Phys. 1993; 98: 5648.
40. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann R, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PM, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision A.1. Gaussian, Inc.: Pittsburgh, PA, 2003.