Abstract
We developed an efficient protocol for the synthesis of thiiranes from oxiranes using a catalytic amount of molecular iodine. The notable features of this procedure are mild reaction conditions, high conversions, short reaction times, economic viability of the reagents, compatibility with various functionalities, and simple experimental/product isolation procedures which make it a useful and attractive process for the synthesis of a range of thiiranes.
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References
DC Ditter AR Katritzky CW Rees (Eds) (1984) Thiiranes and Thiiranes in Comprehensive Heterocyclic Chemistry NumberInSeries7 Pergamon Elmsford, NY 132
K Surendra NS Krishnaveni KR Rao (2004) Tetrahedron Lett 45 6523 Occurrence Handle10.1016/j.tetlet.2004.06.111 Occurrence Handle1:CAS:528:DC%2BD2cXmt1Kju7Y%3D
TR Chan JR Finkenbine (1972) J Am Chem Soc 94 2880 Occurrence Handle10.1021/ja00763a068 Occurrence Handle1:CAS:528:DyaE38XhsFejsrY%3D
Takido T, Kobayashi Y, Itabashi K (1986) Synthesis:779
MO Brimeyer A Mehrota S Quici A Nigam SL Regan (1980) J Org Chem 45 4254 Occurrence Handle10.1021/jo01309a047 Occurrence Handle1:CAS:528:DyaL3cXlvVKjt7s%3D
Yadav JS, Reddy BVS, Baishya G (2002) Synlett:396
B Tamami M Kolahdoozan (2004) Tetrahedron Lett 45 1535 Occurrence Handle10.1016/j.tetlet.2003.12.014 Occurrence Handle1:CAS:528:DC%2BD2cXnsVOqsg%3D%3D
B Kaboudin H Norouzi (2004) Tetrahedron Lett 45 1283 Occurrence Handle10.1016/j.tetlet.2003.11.099 Occurrence Handle1:CAS:528:DC%2BD2cXltFOlsQ%3D%3D
JS Yadav BVS Reddy ChS Reddy K Rajsekhar (2003) J Org Chem 68 2525 Occurrence Handle10.1021/jo026544w Occurrence Handle1:CAS:528:DC%2BD3sXhtlSrsbY%3D
BP Bandgar NS Joshi VT Kamble (2006) Tetrahedron Lett 47 4775 Occurrence Handle10.1016/j.tetlet.2006.03.171 Occurrence Handle1:CAS:528:DC%2BD28XlsVyktrY%3D
Bhosale SV (2007) Synlett:175
Togo H, Iida S (2006) Synlett:2159
RS Bhosale SV Bhosale T Wang PK Zubaidha (2004) Tetrahedron Lett 45 7187 Occurrence Handle10.1016/j.tetlet.2004.08.044 Occurrence Handle1:CAS:528:DC%2BD2cXnt12ksb4%3D
BH Lipshut J Keith (1998) Tetrahedron Lett 39 2495 Occurrence Handle10.1016/S0040-4039(98)00381-5
N Deka DJ Kalita R Borah JC Sharma (1997) J Org Chem 62 1563 Occurrence Handle10.1021/jo961741e Occurrence Handle1:CAS:528:DyaK2sXhs1CqsrY%3D
Vaino AR, Szarek WA (1995) Synlett:1157
JS Yadav BVS Reddy UVS Reddy AD Krishna (2007) Tetrahedron Lett 48 5243 Occurrence Handle10.1016/j.tetlet.2007.05.143 Occurrence Handle1:CAS:528:DC%2BD2sXntF2mtrk%3D
JS Yadav BVS Reddy K Premalatha T Swamy (2005) Tetrahedron Lett 46 2687 Occurrence Handle10.1016/j.tetlet.2005.02.068 Occurrence Handle1:CAS:528:DC%2BD2MXisVCgu78%3D
JS Yadav BVS Reddy PMK Reddy MK Gupta (2005) Tetrahedron Lett 46 8493 Occurrence Handle10.1016/j.tetlet.2005.10.017 Occurrence Handle1:CAS:528:DC%2BD2MXhtFOrs7jF
A Bellomo D Gonzalez (2007) Tetrahedron Lett 48 3047 Occurrence Handle10.1016/j.tetlet.2007.02.113 Occurrence Handle1:CAS:528:DC%2BD2sXjvVajtLc%3D
N Yamada M Mizuochi H Morita (2007) Tetrahedron 63 3408 Occurrence Handle10.1016/j.tet.2007.01.043 Occurrence Handle1:CAS:528:DC%2BD2sXjtVWqtbw%3D
B Das S Reddy M Krishnaiah (2006) Tetrahedron Lett 47 8471 Occurrence Handle10.1016/j.tetlet.2006.09.153 Occurrence Handle1:CAS:528:DC%2BD28XhtFegu7jL
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Correspondence: Jhillu S. Yadav, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
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Yadav, J., Subba Reddy, B., Sengupta, S. et al. Iodine as a mild, efficient, and cost-effective catalyst for the synthesis of thiiranes from oxiranes. Monatsh Chem 139, 1363–1367 (2008). https://doi.org/10.1007/s00706-008-0925-1
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DOI: https://doi.org/10.1007/s00706-008-0925-1