Page 336 - Advanced Organic Chemistry Part B - Reactions & Synthesis

308 Scheme 4.3. Sulfur and Selenium Reagents for Electrophilic Addition Reactions

CHAPTER 4 A. Sulfenylation reagents
Electrophilic Additions 1 a 2 a 3 b 4 c 5 d
to Carbon-Carbon ArSNHPh, BF
) S SCH BF
Multiple Bonds ArSCl RSCl (CH 3 2 + 3 4 – PhS N O 3

6 e O
RSC(CH )
3 3
CO) O
(CF 3 2
B. Selenenylation reagents
7 f 8 g 9 h 10 i 11 j
+
PhSeCl PhSeBr PhSe PF 6 – PhSeO CCF 3 PhSeOSO Ar
2
2
12 k 13 l 14 m 15 n 16 o
PhSeOSO CF 3 PhSeOSO 3 – (PhSe) 2 (PhSe) 2 (PhSe) 2
3
(NH ) S O 8 DDQ PhI(OAc) 2
4 2 2
17 p 18 q 19 r
PhSeO H, H PO 2 O CH(CH )
3 2
2
3
N SePh (CH ) CH SeBr
3 2
O CH(CH )
3 2
a. G. Capozzi, G. Modena, and L. Pasquato in The Chemistry of Sulphenic Acids and Their Derivatives, S. Patai, ed.,
Wiley, Chichester, 1990, Chap. 10.
b. B. M. Trost, T. Shibata, and S. J. Martin, J. Am. Chem. Soc., 104, 3228 (1982).
c. P. Brownbridge, Tetrahedron Lett., 25, 3759 (1984); P. Brownbridge, J. Chem. Soc. Chem. Commun., 1280 (1987);
N. S. Zefirov, N. V. Zyk, A. G. Kutateldze, and S. I. Kolbasenko, Zh. Org. Khim., 23, 227 (1987).
d. L. Benati, P. C. Montevecchi, and P. Spagnolo, J. Chem. Soc., Perkin Trans. 1, 1691 (1990).
e. M.-H. Brichard, M. Musick, Z. Janousek, and H. G. Viehe, Synth. Commun., 20, 2378 (1990).
f. K. B. Sharpless and R. F. Lauer, J. Org. Chem., 39, 429 (1974).
g. T. G. Back, The Chemistry of Organic Selenium and Tellurium Compounds, S. Patai, ed., Wiley, 1987, pp. 91–312.
h. W. P. Jackson, S. V. Ley, and A. J. Whittle, J. Chem. Soc. 1173 (1980).
i. H. J. Reich, J. Org. Chem., 39, 428 (1974).
j. T. G. Back and K. R. Muralidharan, J. Org. Chem. 56, 2781 (1991).
k. S. Murata and T. Suzuki, Tetrahedron Lett., 28, 4297, 4415 (1987).
l. M. Tiecco, L. Testaferri, M. Tingoli, L. Bagnoli, and F. Marini, J. Chem. Soc., Perkin Trans. 1, 1989 (1993).
m. M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli, and D. Bartoli, Tetrahedron Lett., 30, 1417 (1989).
n. M. Tiecco, L. Testaferri, A. Temperinik, L. Bagnoli, F. Marini, and C. Santi, Synlett, 1767 (2001).
o. M. Tingoli, M. Tiecco, L. Testaferri, and Temperini, Synth. Commun., 28, 1769 (1998).
p. D. Labar, A. Krief, and L. Hevesi, Tetrahedron Lett., 3967 (1978).
q. K. C. Nicolaou, N. A. Petasis, and D. A. Claremon, Tetrahedron, 41, 4835 (1985).
r. B. H. Lipshutz and T. Gross, J. Org. Chem., 60, 3572 (1995).
example, the combination phenylselenylphthalimide and trimethylsilyl azide generates
-azido selenides and phenylselenyl chloride used with AgBF and ethyl carbamate
4
give -carbamido selenides.
PhSe
RCH CHR + PhSe-Phthal + (CH ) SiN 3 RCH CHR
3 3
N 3 Ref. 56

56
A. Hassner and A. S. Amarasekara, Tetrahedron Lett., 28, 5185 (1987); R. M. Giuliano and F. Duarte,
Synlett, 419 (1992).