Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines

Vasumathi Desikan; Yonglin Liu; John P. Toscano; William S. Jenks

doi:10.1021/jo702654q

journal article May 29, 2008

Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines

Vasumathi Desikan Yonglin Liu John P. Toscano William S. Jenks

The Journal of Organic Chemistry Vol. 73 No. 12 pp. 4398-4414 · American Chemical Society (ACS)

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References

69

[1]

Borden W. T. Acc. Chem. Res. (2000) 10.1021/ar990030a

[2]

Gritsan N. P. Mol. Supramol. Photochem. (2005) 10.1201/9781420030587.ch5

[3]

Platz M. S. React. Intermed. Chem. (2004)

[4]

Lwowski, W.InReactive Intermediates; Moss, R. A., Jones, M. J., Eds.; Wiley-Interscience: New York, 1985; Vol.3, p305−332.

[5]

Gritsan N. P. Chem. Rev. (2006) 10.1021/cr040055+

[6]

Gritsan N. P. Adv. Phys. Org. Chem. (2001)

[7]

Liu J. J. Org. Chem. (2004) 10.1021/jo048433y

[8]

Garay J.-C. J. Phys. Chem. (1996) 10.1021/jp9528525

[9]

Smolinsky G. J. Am. Chem. Soc. (1962) 10.1021/ja00875a060

[10]

Wasserman E. J. Am. Chem. Soc. (1964) 10.1021/ja01069a049

[11]

Moriarty R. M. J. Am. Chem. Soc. (1966) 10.1021/ja00956a043

[12]

Hoyle C. E. J. Org. Chem. (1983) 10.1021/jo00160a024

[13]

Abramovitch R. A. J. Am. Chem. Soc. (1969) 10.1021/ja01054a065

[14]

Abramovitch R. A. J. Org. Chem. (1972) 10.1021/jo00977a035

[15]

Abramovitch R. A. J. Org. Chem. (1973) 10.1021/jo00959a014

[16]

Abramovitch R. A. J. Org. Chem. (1974) 10.1021/jo00917a013

[17]

Abramovitch R. A. J. Org. Chem. (1974) 10.1021/jo00922a019

[18]

Abramovitch R., A. J. Org. Chem. (1975)

[19]

Abramovitch R. A. Can. J. Chem. (1965) 10.1139/v65-473

[20]

Abramovitch R. A. Can. J. Chem. (1965) 10.1139/v65-473

[21]

Horner L. Chem. Ber. (1963) 10.1002/cber.19630960205

[22]

Lwowski W. J. Am. Chem. Soc. (1965) 10.1021/ja00947a024

[23]

Lwowski W. (1984) 10.1016/b978-0-12-633480-7.50008-0

[24]

Desikan V. J. Org. Chem. (2007) 10.1021/jo071049r

[25]

Stoffregen S. A. J. Am. Chem. Soc. (2008)

[26]

Fujita T. Tetrahedron (2007) 10.1016/j.tet.2007.05.004

[27]

Oae S. (1983)

[28]

Hayashi Y. Tetrahedron Lett. (1972) 10.1016/s0040-4039(01)84752-3

[29]

Hayashi Y. J. Am. Chem. Soc. (1973) 10.1021/ja00797a018

[30]

Harmonic Vibrational Frequencies: An Evaluation of Hartree−Fock, Møller−Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors

Anthony P. Scott, Leo Radom

The Journal of Physical Chemistry 1996 10.1021/jp960976r

[31]

Sankaranarayanan J. Org. Lett. (2008) 10.1021/ol703098q

[32]

Neville A. G. J. Am. Chem. Soc. (1991) 10.1021/ja00005a082

[33]

Brown C. E. Aust. J. Chem. (1995) 10.1071/ch9950363

[34]

Nyquist R. A. Appl. Spectrosc. (1992) 10.1366/0003702924124790

[35]

Harmonic Vibrational Frequencies: An Evaluation of Hartree−Fock, Møller−Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors

Anthony P. Scott, Leo Radom

The Journal of Physical Chemistry 1996 10.1021/jp960976r

[36]

Paquette L. A. J. Org. Chem. (1969) 10.1021/jo01262a015

[37]

As seen below, the excited sulfilimine can produce the nitrene and the isocyanate competitively.

[38]

GC−MS analysis indicated very small quantities of isomeric compounds, also of mass 281. These were interpreted as deriving from small isomeric impurities in the octene.

[39]

Desikan V. J. Org. Chem. (2007) 10.1021/jo071049r

[40]

Lwowski W. (1970)

[41]

Tanner D. Tetrahedron (1994) 10.1016/s0040-4020(01)85546-0

[42]

McConaghy J. S. J. Am. Chem. Soc. (1967) 10.1021/ja00993a037

[43]

Shingaki T. Chem. Lett. (1972) 10.1246/cl.1972.1181

[44]

Breslow D. S. J. Am. Chem. Soc. (1969) 10.1021/ja01037a016

[45]

Pritchina E. A. Phys. Chem. Chem. Phys. (2003) 10.1039/b209775c

[46]

Pritchina E. A. Russ. Chem. Bull. (2005) 10.1007/s11172-005-0287-3

[47]

Zabalov M. V. Russ. Chem. Bull. (2005) 10.1007/s11172-006-0109-2

[48]

Piecuch P. Comput. Phys. Commun. (2002) 10.1016/s0010-4655(02)00598-2

[49]

Renormalized coupled-cluster methods exploiting left eigenstates of the similarity-transformed Hamiltonian

Piotr Piecuch, Marta Włoch

The Journal of Chemical Physics 2005 10.1063/1.2137318

[50]

Nakano H. Chem. Phys. Lett. (1993) 10.1016/0009-2614(93)89016-b

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Details

Published: May 29, 2008
Vol/Issue: 73(12)
Pages: 4398-4414

Authors

V

Vasumathi Desikan

Department of Chemistry, Iowa State University, 3760 Gilman Hall, Ames, Iowa 50011, and Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218

Y

Yonglin Liu

Department of Chemistry, Iowa State University, 3760 Gilman Hall, Ames, Iowa 50011, and Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218

J

John P. Toscano

Department of Chemistry, Iowa State University, 3760 Gilman Hall, Ames, Iowa 50011, and Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218

W

William S. Jenks

Department of Chemistry, Iowa State University, 3760 Gilman Hall, Ames, Iowa 50011, and Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218

Cite This Article

Vasumathi Desikan, Yonglin Liu, John P. Toscano, et al. (2008). Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines. The Journal of Organic Chemistry, 73(12), 4398-4414. https://doi.org/10.1021/jo702654q

Photochemistry of N-Acetyl-, N-Trifluoroacetyl-, N- Mesyl-, and N-Tosyldibenzothiophene Sulfilimines

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