Mild and Efficient Hydrolysis of Aromatic Thioacetals/Thioketals using o-Iodoxybenzoic acid (IBX) in Presence of β- Cyclodextrin in Water

N. Srilakshmi Krishnaveni; K. Surendra; Y. V. D. Nageswar; K. Rama Rao

doi:10.1055/s-2003-41055

SHORTPAPER

Mild and Efficient Hydrolysis of Aromatic Thioacetals/Thioketals using o-Iodoxybenzoic acid (IBX) in Presence of β- Cyclodextrin in Water

N. Srilakshmi Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. Rama Rao*
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India
e-Mail: ramaraok@iict.res.in;

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient and user-friendly procedure has been developed for the hydrolysis of thioacetals/thioketals to the corresponding carbonyl compounds in impressive yields with o-iodoxybenzoic acid (IBX) in presence of β-cyclodextrin (β-CD) in water under neutral conditions at room temperature.

Key Words

hydrolysis - thioacetals - thioketals - o-iodoxybenzoic acid - β-cyclodextrin - water

Volltext

Referenzen

References

<A NAME="RZ06703SS-1A">1a</A> Grieco P. Organic Synthesis in Water Blackie Academic & Professional; London: 1998.

<A NAME="RZ06703SS-1B">1b</A> Li C.-J. Chem. Rev. 1993, 93: 2023

<A NAME="RZ06703SS-1C">1c</A> Lubineau A. Auge J. Queneau Y. Synthesis 1994, 741

<A NAME="RZ06703SS-2A">2a</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd Ed.: John Wiley & Sons; New York: 1999.

<A NAME="RZ06703SS-2B">2b</A> Kocienski PJ. Protecting Groups Thieme; Stuttgart: 1994.

<A NAME="RZ06703SS-3A">3a</A> Rychnovsky SD. Chem. Rev. 1995, 95: 2021

<A NAME="RZ06703SS-3B">3b</A> Smith AB. Condon SM. McCauley JA. Acc. Chem. Res. 1998, 31: 35

<A NAME="RZ06703SS-3C">3c</A> Metzner P. Thuiller A. Sulfur Reagents in Organic Synthesis Academic Press; New York: 1994. p.12-19

<A NAME="RZ06703SS-3D">3d</A> Kocienski PJ. Protecting Groups Thieme; Stuttgart: 1994. p.156-170

<A NAME="RZ06703SS-4">4</A> Grobel B.-T. Seebach D. Synthesis 1977, 357

<A NAME="RZ06703SS-5A">5a</A> Eliel EL. Morris-Natschke S. J. Am. Chem. Soc. 1984, 106: 2937

<A NAME="RZ06703SS-5B">5b</A> Bulman-Page PC. Van-Niel MB. Prodger J. Tetrahedron 1989, 45: 7643

<A NAME="RZ06703SS-5C">5c</A> Seebach D. Synthesis 1969, 17

<A NAME="RZ06703SS-6">6</A> Petti GW. Van Tamelen EE. Org. React. 1962, 12: 356

<A NAME="RZ06703SS-7A">7a</A> Ravindranathan T. Chavan SP. Dantale SW. Tetrahedron Lett. 1995, 36: 2285

<A NAME="RZ06703SS-7B">7b</A> Chavan SP. Soni P. Kamat SK. Synlett 2001, 1251

<A NAME="RZ06703SS-7C">7c</A> Schmittel M. Levis M. Synlett 1996, 315

<A NAME="RZ06703SS-7D">7d</A> Oishi T. Kamemoto K. Ban Y. Tetrahedron Lett. 1972, 12: 1085

<A NAME="RZ06703SS-7E">7e</A> Hirano M. Ukawa K. Yakabe S. Clark JH. Levis M. Synlett 1996, 858

<A NAME="RZ06703SS-8A">8a</A> Mandai T. Takeshita M. Kawada M. Otera J. Chem. Lett. 1984, 1259

<A NAME="RZ06703SS-8B">8b</A> Nishide K. Yokota K. Nakamura D. Sumiya T. Node M. Tetrahedron Lett. 1993, 34: 3425

<A NAME="RZ06703SS-8C">8c</A> Karimi B. Seradj H. Tabae MH. Synlett 2000, 1798

<A NAME="RZ06703SS-8D">8d</A> Mehta G. Uma R. Tetrahedron Lett. 1996, 37: 1897

<A NAME="RZ06703SS-8E">8e</A> Fuji K. Ichikawa K. Fujitha E. Tetrahedron Lett. 1978, 18: 3561

<A NAME="RZ06703SS-8F">8f</A> Emerson DW. Winberg H. Tetrahedron Lett. 1971, 11: 3445

<A NAME="RZ06703SS-9A">9a</A> Ho T.-L. Ho HC. Wong CM. J. Chem. Soc., Chem. Commun. 1972, 791

<A NAME="RZ06703SS-9B">9b</A> Stork G. Zhao K. Tetrahedron Lett. 1989, 30: 287

<A NAME="RZ06703SS-10">10</A> Yadav JS. Reddy BVS. Raghavendra S. Satyanarayana M. Tetrahedron Lett. 2002, 43: 4679

<A NAME="RZ06703SS-11A">11a</A> Corey EJ. Erickson BW. J. Org. Chem. 1971, 36: 3553

<A NAME="RZ06703SS-11B">11b</A> Vedejs E. Fuchs PL. J. Org. Chem. 1971, 36: 366

<A NAME="RZ06703SS-11C">11c</A> Oishi T. Kamemoto K. Ban Y. Tetrahedron Lett. 1972, 13: 1085

<A NAME="RZ06703SS-11D">11d</A> Fetizon M. Jurion M. J. Chem. Soc., Chem. Commun. 1972, 382

<A NAME="RZ06703SS-11E">11e</A> Wu Y. Shen X. Huang J.-H. Tang C.-J. Liu H.-H. Hu Q. Tetrahedron Lett. 2002, 43: 6443

<A NAME="RZ06703SS-12A">12a</A> Surendra K. Krishnaveni NS. Reddy MA. Nageswar YVD. Rao KR. J. Org. Chem. 2003, 68: 2058

<A NAME="RZ06703SS-12B">12b</A> Krishnaveni NS. Surendra K. Reddy MA. Nageswar YVD. Rao KR. J. Org. Chem. 2003, 68: 2018

<A NAME="RZ06703SS-12C">12c</A> Reddy MA. Surendra K. Bhanumathi N. Rao KR. Tetrahedron 2002, 58: 6003

<A NAME="RZ06703SS-12D">12d</A> Reddy MA. Bhanumathi N. Rao KR. Tetrahedron Lett. 2002, 43: 3237

<A NAME="RZ06703SS-12E">12e</A> Reddy LR. Reddy MA. Bhanumathi N. Rao KR. Synlett 2000, 339

<A NAME="RZ06703SS-12F">12f</A> Reddy MA. Reddy LR. Bhanumathi N. Rao KR. New J. Chem. 2001, 25: 359

<A NAME="RZ06703SS-13A">13a</A> Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997.

<A NAME="RZ06703SS-13B">13b</A> Wirth T. Hirt UH. Synthesis 1999, 1271

<A NAME="RZ06703SS-14A">14a</A> Firouzabadi H. Jamalian A. Karimi B. Bull. Chem. Soc. Jpn. 2002, 75: 1761

<A NAME="RZ06703SS-14B">14b</A> Shirini F. Zolfigol MA. Mallakpour B. Mallakpour SE. Hatipour AR. Baltork IM. Tetrahedron Lett. 2002, 43: 1555

<A NAME="RZ06703SS-14C">14c</A> Firouzabadi H. Mohammadpoor-Baltork I. Synth. Commun. 1994, 24: 489

<A NAME="RZ06703SS-14D">14d</A> Salchi P. Khodaei MM. Goodarzi M. Synth. Commun. 2002, 32: 1259