CC BY 4.0 · SynOpen 2023; 07(02): 267-271
DOI: 10.1055/s-0040-1720071
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Recent Applications of Hexamethyldisilathiane (TMS2S) in Organic Synthesis

Damien Hazelard
,


Abstract



Publication History

Received: 14 April 2023

Accepted after revision: 15 May 2023

Article published online:
05 June 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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  • References and Notes

    • 1a Eaborn C. Nature 1950; 165: 1686
    • 1b Eaborn C. J. Chem. Soc. 1950; 165: 3077
    • 1c So J.-H, Boudjouk P, Hong HH, Weber WP. Inorg. Synth. 1992; 29: 30
  • 2 For others methods for the preparation of TMS2S, see: Curphey TJ. Phosphorus, Sulfur, Silicon Relat. Elem. 2001; 173: 123
  • 3 Sigma-Aldrich (accessed March 16, 2023): https://www.sigmaaldrich.com/FR/en/product/aldrich/283134

    • For selected reviews, see:
    • 4a Matulenko MA, Degl’Innocenti A, Capperucci A. Bis(trimethylsilyl) sulfide . In Encyclopedia of Reagents for Organic Synthesis . Paquette L. Wiley; New York: 2007
    • 4b Degl’Innocenti A, Capperucci A, Castagnoli G, Malesci I. Synlett 2005; 1965
    • 4c Degl’Innocenti A, Capperucci A, Nocentini T, Castagnoli G, Malesci I, Cerreti A. Phosphorus, Sulfur, Silicon Relat. Elem. 2005; 180: 1247

      For recent examples, see:
    • 5a Rojas-León I, Christmann J, Schwan S, Ziese F, Sanna S, Mollenhauer D, Rosemann NW, Dehnen S. Adv. Mater. 2022; 34: 2203351
    • 5b Liu LJ, Zhang JW, Asas M, Whang Z.-Y, Zhang S.-Q, Mak TC. W. Chem. Commun. 2021; 57: 5586

      See for examples:
    • 6a Sato Y, Nishimura M, Kawaguchi S, Nomoto A, Ogawa A. Chem. Eur. J. 2019; 25: 6797
    • 6b Graham CM. E, Pritchard TE, Boyle PD, Valjus J, Tuononen HM, Ragogna PJ. Angew. Chem. Int. Ed. 2017; 56: 6236
    • 6c Graham CM. E, Macdonald CL. B, Boyle PD, Wisner JA, Ragogna PJ. Chem. Eur. J. 2018; 24: 743
  • 7 Search run on Scifinder March 16, 2023.
  • 8 Hu J, Fox MA. J. Org. Chem. 1999; 64: 4959

    • For recent examples, see:
    • 9a Jayaraman J, Ganapathy AS, Thanikachalam V, Palanivel J, Sekar P. J. Phys. Org. Chem. 2018; 31: e3796
    • 9b Kong R, Xiao Z, Xie F, Jiang J, Ding L. New J. Chem. 2017; 41: 2895
    • 9c Kothur RR, Patel BA, Cragg PJ. Chem. Commun. 2017; 53: 9078
    • 9d Wójcik MM, Wróbel J, Jańczuk ZZ, Mieczkowski J, Górecka E, Choi J, Cho M, Pociecha D. Chem. Eur. J. 2017; 23: 8912
    • 9e Rahman ML, Biswas TK, Sarkar SM, Yusoff MM, Yuvaraj AR, Kumar S. J. Colloid Interface Sci. 2016; 478: 384
    • 9f Sun J, Li W, Xiao L, Yu G, Shi J. RSC Adv. 2016; 6: 62200
    • 9g Olshansky JH, Ding TX, Lee YV, Leone SR, Alivisatos AP. J. Am. Chem. Soc. 2015; 137: 15567
    • 9h Liu Y, Najafabadi BK, Fard MA, Corrigan JF. Angew. Chem. Int. Ed. 2015; 54: 4832
  • 10 Kizling M, Dzwonek M, Nowak A, Tymecki L, Stolarczyk K, Więckowska A, Bilewicz B. Nanomaterials 2020; 10: 1434

    • See also:
    • 11a Reddy PV. G, Lin Y.-W, Chang H.-T. ARKIVOC 2007; (xvi): 113
    • 11b Gopidas KR, Whitesell JK, Fox MA. J. Am. Chem. Soc. 2003; 125: 14168
  • 12 Ogiwara Y, Takano K, Horikawa S, Sakai N. Molecules 2018; 23: 1339
  • 13 Nie Z, Chiou M.-F, Cui J, Qu Y, Zhu X, Jian W, Xiong H, Li Y, Bao H. Angew. Chem. Int. Ed. 2022; 61: e202202077
  • 14 Sakai N, Horikawa S, Ogiwara Y. Synthesis 2018; 50: 565
  • 15 Degl’Innocenti A, Capperucci A, Cerreti A, Pollicino S, Scapecchi S, Malesci I, Castagnoli G. Synlett 2005; 3063
    • 16a Tanini D, Borgogni C, Capperucci A. New J. Chem. 2019; 43: 6388
    • 16b Tanini D, Barchielli G, Benelli F, Degl’Innocenti A, Capperucci A. Phosphorus, Sulfur, Silicon Relat. Elem. 2015; 190: 1265
  • 17 For a review on ring opening of 1,6-anhydrosugars, see: Hazelard D, Compain P. Eur. J. Org. Chem. 2021; 3501
  • 18 Zhu X, Dere RT, Jiang J, Zhang L, Wang X. J. Org. Chem. 2011; 76: 10187
  • 19 Céspedes DávilaM. F, Schneider JP, Godard A, Hazelard D, Compain P. Molecules 2018; 23: 914
  • 20 Tardieu D, Céspedes DávilaM. F, Hazelard D, Compain P. Synthesis 2018; 50: 3927
  • 21 Ogiwara Y, Maeda H, Sakai N. Synlett 2018; 19: 655
  • 22 Sakai N, Maeda H, Ogiwara Y. Synthesis 2019; 51: 2323
  • 23 Nakajima T, Takeuchi R, Oomori K, Ishida K, Ogiwara Y, Sakai N. Synthesis 2023; 55: 779
  • 24 Tanini D, Angeli A, Capperucci A. Phosphorus, Sulfur, Silicon Relat. Elem. 2016; 191: 156
  • 25 Tanini D, Trapani F, Capperucci A. J. Sulfur Chem. 2020; 41: 635
  • 26 Nakajima T, Takano K, Maeda H, Ogiwara Y, Sakai N. Chem. Asian J. 2021; 16: 4103