Trimethylchlorosilane (TMSCl) and Cyanuric Chloride (CC) Catalyzed Efficient­ Oxidative Coupling of Thiols with Dimethylsulfoxide

Abstract

Different types of thiols were rapidly and efficiently converted to disulfides using DMSO in the presence of catalytic amounts of either trimethylchlorosilane (TMSCl) or cyanuric chloride­ (CC).

thiols - disulfides - oxidative coupling

References

<A NAME="RZ09802SS-1">1</A> Jocelyn DC. In Biochemistry of the Thiol Groups   Academic Press; New York: 1992. 

<A NAME="RZ09802SS-2">2</A> Capozzi G. Modena G. In The Chemistry of the Thiol Group   Patai S. Wiley; New York: 1974.  Part 2. p.785 

<A NAME="RZ09802SS-3A">3a</A> Noureldin MC. Hendry J. Lee DG. Synthesis  1998,  1587 

<A NAME="RZ09802SS-3B">3b</A> Firouzabadi H. Abbassi M. Karimi B. Synth. Commun.  1999,  29:  2527 

<A NAME="RZ09802SS-3C">3c</A> Kesavan V. Bonnet-Delpon D. Begue JP. Synthesis  2000,  223 

<A NAME="RZ09802SS-3D">3d</A> Fujihara H. Akashi R. Furukawa N. Bull. Chem. Soc. Jpn.  1989,  62:  616 

<A NAME="RZ09802SS-3E">3e</A> Meshram HM. Kache R. Synth. Commun.  1997,  27:  2403 

<A NAME="RZ09802SS-3F">3f</A> Lu G. Zhang Y. Synth. Commun.  1998,  28:  4479 

<A NAME="RZ09802SS-3G">3g</A> McKillop A. Koyuneu D. Tetrahedron Lett.  1990,  31:  5007 

<A NAME="RZ09802SS-3H">3h</A> Karimi B. Zareyee D. Synlett  2002,  346 

<A NAME="RZ09802SS-4A">4a</A> Iranpoor N. Salehi P. Shiriny F. Org. Prep. Proced. Int.  1995,  27:  216 

<A NAME="RZ09802SS-4B">4b</A> Scrivens G. Gilbert BC. Lee CPT. J. Chem. Soc., Perkin Trans 2  1995,  995 

<A NAME="RZ09802SS-4C">4c</A> Iranpoor N. Zeynizadeh B. Synthesis  1999,  49 

<A NAME="RZ09802SS-4D">4d</A> Iranpoor N. Firouzabadi H. Zolfigol MA. Synth. Commun.  1998,  28:  367 

<A NAME="RZ09802SS-4E">4e</A> Raghavan S. Rajender A. Joseph SC. Rasheed MA. Synth. Commun.  2001,  31:  1477 

<A NAME="RZ09802SS-4F">4f</A> Choi J. Yoon NM. J. Org. Chem.  1995,  60:  3266 

<A NAME="RZ09802SS-4G">4g</A> Arterburn JB. Perry MC. Nelson SL. Dible BR. Holguin MS. J. Am. Chem. Soc.  1997,  119:  9309 

<A NAME="RZ09802SS-5A">5a</A> Yiannios CN. Karabinos JV. J. Org. Chem.  1963,  28:  3246 

<A NAME="RZ09802SS-5B">5b</A> Wallace TJ. Chem. Ind (London)  1964,  501 

<A NAME="RZ09802SS-5C">5c</A> Wallace TJ. J. Am. Chem. Soc.  1964,  86:  2018 

<A NAME="RZ09802SS-5D">5d</A> Wallace TJ. Mahon JJ. J. Am. Chem. Soc.  1964,  86:  4099 

<A NAME="RZ09802SS-5E">5e</A> Wallace TJ. Mahon JJ. J. Org. Chem.  1965,  30:  1502 

<A NAME="RZ09802SS-5F">5f</A> Wallace TJ. Weiss HA. Chem. Ind. (London)  1966,  1558 

<A NAME="RZ09802SS-6">6</A> Mancuso AJ. Swern D. Synthesis  1981,  165 

<A NAME="RZ09802SS-7">7</A> Senier A. Ber.  1886,  19:  311 

<A NAME="RZ09802SS-8">8</A> Venkataraman K. Wagle DR. Tetrahedron Lett.  1979,  3037 

<A NAME="RZ09802SS-9">9</A> Venkataraman K. Wagle DR. Tetrahedron Lett.  1980,  21:  1893 

<A NAME="RZ09802SS-10">10</A> Falorni M. Porcheddu A. Taddei M. Tetrahedron Lett.  1999,  40:  4395 

<A NAME="RZ09802SS-11">11</A> Forbes DC. Barrett EJ. Lewis DL. Smith MC. Tetrahedron Lett.  2000,  41:  9943 

<A NAME="RZ09802SS-12">12</A> Manhas MS. Bose AK. Kajavi MS. Synthesis  1981,  209 

<A NAME="RZ09802SS-13">13</A> Olah GA. Fung AP. Gupta BGB. Narang SC. Synthesis  1980,  221 

<A NAME="RZ09802SS-14">14</A> De Luca L. Giacomelli G. Porcheddu A. Org. Lett.  2002,  4:  553 ; and references cited therein

<A NAME="RZ09802SS-15">15</A> De Luca L. Giacomelli G. Porcheddu A. J. Org. Chem.  2001,  66:  7907 

<A NAME="RZ09802SS-16">16</A> Groebel W. Chem. Ber.  1960,  93:  284 

<A NAME="RZ09802SS-17">17</A> Cohen VI. Helv. Chim. Acta  1976,  59:  840 

<A NAME="RZ09802SS-18">18</A> Liu KT. Tong YC. Synthesis  1978,  669 

<A NAME="RZ09802SS-19">19</A> Ramadas K. Srinivasan N. Synth. Commun.  1995,  25:  227