Abstract
Benzyltriphenylphosphonium peroxodisulfate has been found to be an effective reagent for the oxidative deprotection of trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers, ethylene acetals and ketals to their corresponding carbonyl compounds in excellent yields. Selective oxidative deprotection of TMS ethers in the presence of THP ethers and ethylene acetals (ketals) makes this method a useful and practical procedure in organic synthesis.
References
1.
Greene T.W.
, and
Wutz P. G. M.
, Protective Groups in Organic Synthesis , 2nd ed., John Wiley , New York 1991 .
2.
Lalonde M.
, and
Chan T. H.
, Synthesis , 1985 , 817 and references cited therein.
3.
Firouzabadi H.
, and
Karimi B.
, Synth. Commun. , 1993 , 23 , 1633 .
4.
Maity G.
, and
Roy S. C.
, Synth. Commun. , 1993 , 23 , 1667 .
5.
Upadhya T. T.
,
Daniel T.
,
Sudalai A.
,
Ravindranathan T.
, and
Sabu K. R.
, Synth. Commun. , 1996 , 26 , 4539 .
6.
Ballini R.
,
Bigi F.
,
Carloni S.
,
Maggi R.
, and
Sartori G.
, Tetrahedron Lett. , 1997 , 38 , 4169 .
7.
Babu B.S.
, and
Balasubramanian K. K.
, Tetrahedron Lett. , 1998 , 39 , 9287 .
8.
Davis K.J.
,
Bhalerao U. T.
, and
Rao B. V.
, Synth. Commun. , 1999 , 29 , 1679 .
9.
Baker R.
,
Rao V. B.
,
Ravenscroft P. D.
, and
Swain C. J.
, Synthesis , 1983 , 572 .
10.
Olah G.A.
,
Gupta B. G. B.
, and
Fung A. P.
, Synthesis , 1980 , 897 .
11.
Sonnet P.E.
, Org. Prep. Proced. Int. , 1978 , 10 , 91 .
12.
Parish E.J.
,
Kizito S. A.
, and
Heidepriem R. W.
, Synth. Commun. , 1993 , 23 , 223 .
13.
Firouzabadi H.
, and
Mohammadpoor-Baltork I.
, Synth. Commun. , 1994 , 24 , 1065 .
14.
Firouzabadi H.
, and
Shiriny F.
, Synth. Commun. , 1996 , 26 , 423 .
15.
Firouzabadi H.
,
Badparva H.
, and
Sardarian A. R.
, Iran J. Chem. & Chem. Eng. , 1998 , 17 , 33 .
16.
Meskens F.A. J.
, Synthesis , 1981 , 501 and references cited therein.
17.
Li T.S.
,
Li S. H.
,
Li J. T.
, and
Li H. Z.
, J. Chem. Res. (S) , 1997 , 26 .
18.
Bandgar B.P.
,
Kulkarni M. M.
, and
Wadgaonkar P. P.
, Synth. Commun. , 1997 , 27 , 627 .
19.
Kalita D.J.
,
Borah R.
, and
Sarma J. C.
, Tetrahedron Lett. , 1998 , 39 , 4573 .
20.
Ballini R.
,
Bosica G.
,
Frullanti B.
,
Maggi R.
,
Sartori G.
, and
Schroer F.
, Tetrahedron Lett. , 1998 , 39 , 1615 .
21.
Gautier E.C. L.
,
Graham A. E.
,
McKillop A.
,
Standen S. P.
, and
Taylor R. J. K.
, Tetrahedron Lett. , 1997 , 38 , 1881 .
22.
Marcantoni E.
, and
Nobili F.
, J. Org. Chem. , 1997 , 62 , 4183 .
23.
Saravanan P.
,
Chandrasekhar M.
,
Anand R. V.
, and
Singh V. K.
, Tetrahedron Lett. , 1998 , 39 , 3091 .
24.
Mohammadpoor-Baltork I.
,
Hajipour A. R.
, and
Mohammadi H.
, Bull. Chem. Soc. Jpn. , 1998 , 71 , 1649 .
25.
Mohammadpoor-Baltork I.
, and
Pouranshirvani Sh.
, Synthesis , 1997 , 756 .
26.
Mohammadpoor-Baltork I.
, and
Kharamesh B.
, J. Chem. Res. (S) , 1998 , 146 .
27.
Mohammadpoor-Baltork I.
, and
Nourozi A. R.
, Synthesis , 1999 , 487 .
