1864
A. Bhattacharya et al. / Tetrahedron Letters 47 (2006) 1861–1864
4. (a) Hwuk, J. R.; Wong, F. F.; Shiao, M.-J. J. Org. Chem.
Acknowledgements
1992, 57, 5254; (b) Shiao, J.-J.; Long-Li, L.; Wei-Shan, K.;
Lin, P.-Y.; Hwu, J. R. J. Org. Chem. 1993, 58, 4742; (c) The
formation of nitrosobenzene via an alternate pathway
involving the nucleophilic attack of RS(À) on the oxygen of
the nitro functionality can not be ruled out.
Financial support provided by the Petroleum Research
Fund (PRF), National Institute of Health (NIH), Welch
Foundation, and Bristol Myers Squibb Corporation is
gratefully acknowledged.
5. (a) Average bond energy of C–S is 65 kcal/mol, C–C is
83 kcal/mol and C–Si is 83 kcal/mol; data obtained from
Michigan State University–Organic home page website
For analogous O- to C-acyl migration, see Baker–Venkata-
raman rearrangement: (b) Bowden, K.; Chehel-Amiran, M.
J. Chem. Soc., Perkin Trans. 2 1986, 2039.
6. An alternate mechanism could involve S–S bond formation
thereby delivering two electrons in the form of a hydride
(HÀ). The S–S bond formation has precedence in peptide
chemistry of cysteine. The resulting dithiane can act as an
effective acylating agent.
References and notes
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9. (a) All of the compounds gave a 13C resonance of
169 2 ppm, indicative of the amide carbon and
a
resonance at 24 2 ppm indicative of the acetamide
methyl. The 13C and 1H NMR spectra were consistent
with the products in coupling and chemical shift data; (b)
For all the compounds GC–MS analysis (Shimadzu
QP5050A) in the EI mode provided similarity index match
of >90% compared to the authentic samples in the NIST-98
database.
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