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Synthesis 2002(15): 2259-2265
DOI: 10.1055/s-2002-34838
DOI: 10.1055/s-2002-34838
PAPER
© Georg Thieme Verlag Stuttgart · New York
CAN Mediated Reaction of Aryl
Sulfinates with Alkenes and Alkynes:
Synthesis of Vinyl
Sulfones, β-Iodovinyl Sulfones and Acetylenic Sulfones
Further Information
Received
30 April 2002
Publication Date:
21 October 2002 (online)
Publication History
Publication Date:
21 October 2002 (online)
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Abstract
Cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate afforded the corresponding acetylenic sulfones in high yields.
Key words
cerium(IV) ammonium nitrate - sulfonylation - aryl alkenes - alkenes - acetylenes - vinyl sulfones - β-iodovinyl sulfones - acetylenic sulfones
-
1a
Heiba EI.Dessau RM. J. Am. Chem. Soc. 1971, 93: 524 -
1b
Baciocchi E.Ruzziconi R. Synth. Commun. 1988, 18: 1841 -
1c
Baciocchi E.Ruzziconi R. J. Org. Chem. 1986, 51: 1645 - 2
Nair V.Mathew J.Prabhakaran J. Chem. Soc. Rev. 1997, 127 ; and references cited therein - 3
Trahanovsky WS.Robbins MD. J. Am. Chem. Soc. 1971, 93: 5256 - 4
Lemieux RU.Ratcliffe RM. Can. J. Chem. 1979, 93: 5256 - 5
Nair V.Nair LG. Tetrahedron Lett. 1998, 39: 4585 - 6
Nair V.George TG.Nair LG.Panicker SB. Tetrahedron Lett. 1999, 40: 1105 - 7
Nair V.George TG. Tetrahedron Lett. 2000, 41: 3199 - 8
Nair V.Nair LG.George TG.Augustine A. Tetrahedron 2000, 56: 7607 - 9
Nair V.Augustine A.George TG. Eur. J. Org. Chem. 2002, 2363 - 10
Nair V.George TG.Sheeba V.Augustine A.Balagopal L.Nair LG. Synlett 2000, 1597 - 11
Nair V.Augustine A.George TG.Nair LG. Tetrahedron Lett. 2001, 42: 6763 - 12
Popoff IC.Denver JL. J. Org. Chem. 1969, 34: 1128 - 13
Ley SV.Simpkins NS. J. Chem. Soc., Chem Commun. 1983, 1281 - 14
Gancarz RA.Kice JL. Tetrahedron Lett. 1980, 4155 -
15a
Asscher M.Vofsi D. J. Chem. Soc. 1964, 4962 -
15b
Asscher M.Vofsi D. J. Chem. Soc., Perkin Trans. 1 1972, 1543 -
15c
Hopkins PB.Fuchs PL. J. Org. Chem. 1978, 43: 1208 -
16a
Fuchs PL.Braish TF. Chem. Rev. 1986, 86: 903 -
16b
De Lucci O.Pasquato L. Tetrahedron 1988, 44: 6755 -
17a
Truce WE.Heuring DL.Wolf GC. J. Org. Chem. 1974, 39: 238 -
17b
Iwata N.Morioka T.Kobayashi T.Asada T.Kinoshita H.Inomata K. Bull. Chem. Soc. Jpn. 1992, 65: 1379 -
17c
Harwood LM.Julia M.Thuillier GLe. Tetrahedron 1980, 36: 2483 -
17d
Short KM.Ziegler CB. Tetrahedron Lett. 1993, 34: 71 -
17e
Zoller T.Uguen D.Cian AD.Fischer J. Tetrahedron Lett. 1998, 39: 8089 -
18a
Truce WE.Goralski CT.Christensen LW.Bavry RH. J. Org. Chem. 1970, 35: 4217 -
18b
Amiel Y. Tetrahedron Lett. 1971, 661 -
18c
Amiel Y. J. Org. Chem. 1971, 36: 3691 -
18d
Amiel Y. J. Org. Chem. 1974, 39: 3867 -
18e
Truce WE.Wolf GC. J. Chem. Soc., Chem. Commun. 1969, 150 -
19a
Gancarz RA.Kice JL. J. Org. Chem. 1981, 46: 4899 -
19b
Inomata K.Sasaoka S.Morioka T.Kobayashi T.Tanaka Y.Igarashi S.Ohtani T.Kinoshita S.Kotake H. Bull. Chem. Soc. Jpn. 1987, 60: 1767 -
19c
Duan DH.Huang X. Synlett 1999, 317 - 20
Kamigata N.Sawada H.Kobayashi M. J. Org. Chem. 1983, 48: 3793 -
21a
Jang WB.Jeon HJ.Oh DY. Synth. Commun. 1998, 28: 1253 -
21b
Lee WJ.Lee C.-W.Jung JH.Oh DY. Synth. Commun. 2000, 30: 279 -
22a
Narasaka K.Mochizuki T.Hayakawa S. Chem. Lett. 1994, 1705 -
22b
Mochizuki T.Hayakawa S.Narasaka K. Bull. Chem. Soc. Jpn. 1996, 69: 2517 -
22c
Bordwell FG.Kern RJ. J. Am. Chem. Soc. 1955, 77: 1141 - 23
Truce WE.Wolf GC. J. Org. Chem. 1971, 36: 1727 - 24
Harwood LM.Julia M.Le Thuillier G. Tetrahedron 1980, 36: 2483 -
25a
Suzuki H.Abe H. Tetrahedron Lett. 1996, 37: 3717 -
25b
Lee JW.Oh DY. Synlett 1990, 290