Abstract
The current section presents an overview of the fundamental aspects of thiocarbonyl compounds, such as thioaldehydes and thioketones. Firstly, a theoretical approach and a physical-organic experimental approach disclose their properties. Secondly, their synthetic reactions are introduced. Finally, a focus is given to their synthetic applications, including nucleophilic and electrophilic reactions, as well as concerted reactions.
Similar content being viewed by others
References
Collier SJ (2004) Sci Synth 27:177
Cooper NJ (2005) In: Katritzky AR, Taylor RJK (eds) Comprehensive organic functional group transformations II, vol 3. Elsevier, Oxford, p 355
Dabdoub MJ (2004) Sci Synth 27:215
Okazaki R, Ishii A, Fukuda N, Oyama H, Inamoto N (1982) J Chem Soc Chem Commun 1982:1187
Okazaki R, Ishii A, Inamoto N (1987) J Am Chem Soc 109:279
Takeda N, Tokitoh N, Okazaki R (1997) Chem Eur J 3:62
Ando W, Ohtani T, Suzuki T, Kabe Y (1991) J Am Chem Soc 113:7782
Dabrowski J, Kamienska-Trela K, Kozerski L (1975) Org Magn Res 6:499
MaKenzie S, Reid DH (1970) J Chem Soc (C) 1970:145
Reva I, Nowak MJ, Lapinski L, Fausto R (2015) Phys Chem Chem Phys 17:4888
Yamaguchi M, Shida T (2016) J Phys Chem A 120:3570
von Ochmann M, Ahnen I, Cordones AA, Hussain A, Lee JH, Hong K, Adamczyk K, Vendrell O, Kim TK, Schoenlein RW, Huse N (2017) J Am Chem Soc 139:4797
Kumar M, Francisco JS (2017) Chem Eur J 23:2522
Zhang Y, Zhang W, Zhang T, Tian W, Wang W (2012) Comp Theor Chem 994:65
Zhang T, Wang R, Zhou L, Wang Z, Xu Q, Min S, Wang W (2014) RSC Adv 4:62835
Krystkowiak E, Bachorz RA, Maciejewski A (2016) Phys Chem Chem Phys 18:49
Matczak P, Domagała M, Domagała S (2016) Struct Chem 27:855
Saad ZB, Chong SX, Wong ZX, Abdallah HH, Al-Saadi AA (2011) J Mol Struct 1006:655
He J-Y, Long Z-W, Zhang J-S (1057) J Struct Chem 2011:52
Elias RS, Saeed BA, Muslem DK (2012) J Appl Sci 9:152
Trung NT, Hue TT, Nguyen MT (2009) J Phys Chem A 113:3245
Trung NT, Hung NP, Hue TT, Nguyen MT (2011) Phys Chem Chem Phys 13:14033
Raissi H, Nadim ES, Yoosefian M, Farzad F, Ghiamati E, Nowroozi AR, Fazli M, Amoozadeh A (2010) J Mol Struct 960:1
Nowroozi A, Roohi H, Hajiabadi H, Raissi H, Khalilinia E, Birgan MN (2011) Comp Theor Chem 963:517
Nowroozi A, Roohi H, Poorsargol M, Jahani PM, Hajiabadi H, Raissi H (2011) Int J Quantum Chem 111:3008
Shakerzadeh E, Tahmasebi E (2014) Comp Theor Chem 1039:21
Pietrzak M, Dobkowski J, Gorski A, Gawinkowski S, Kijak M, Luboradzki R, Hansen PE, Waluk J (2014) Phys Chem Chem Phys 16:9128
Nowroozi A, Sarhadinia S, Masumian E, Nakhaei E (2014) Struct Chem 25:1359
Pandiyan BV, Deepa P, Kolandaivel P (2015) Phys Chem Chem Phys 17:27496
Si MK, Ganguly B (2016) New J Chem 40:9132
Nowroozi A, Masumian E (2017) Struct Chem 28:587
Rad OR, Nowroozi A (2017) Struct Chem 28:1141
Sklenak S, Apeloig Y, Rappoport Z (2000) J Chem Soc Perkin Trans 2:2269
Ruiz DL, Schiavoni M, Laurella SL, Giussi JM, Furlong JJP (2011) Spectrochim Acta Part A 78:1397
Chuang C-H, Lien M-H (2004) J Phys Chem A 108:1790
Guillemin JC, Riague EH, Gal JF, Maria PC, Mó O, Yanez M (2005) Chem Eur J 11:2145
Saeed BA, Elias RS, Musad EA (2011) Am J Appl Sci 8:762
Zborowski KK (2012) Chem Phys Lett 545:144
Karton A, O’Reilly RJ, Radom L (2012) J Phys Chem A 116:4211
Cortes-Santiago A, Navarrete-Lopez AM, Vargas R, Garza J (2017) J Phys Org Chem 30:e3624
Ozturk T, Ertas E, Mert O (2010) Chem Rev 110:3419
Jesberger M, Davis TP, Barner L (2003) Synthesis 2003:1929
Rodrigo R, de Moreira M (2008) Synlett 2008:463
Kayukova LA, Praliyev KD, Gut’yar VG, Baitursynova GP (2015) Russ J Org Chem 51:148
Kutsumura N, Ohshita R, Horiuchi J, Tateno K, Yamamoto N, Saitoh T, Nagumo Y, Kawai H, Nagase H (2017) Tetrahedron 73:5214
Berman J, Pettersson B, Hasimbegovic V, Svensson PH (2011) J Org Chem 76:1546
Cho D, Ahn J, De Castro KA, Ahn H, Rhee H (2010) Tetrahedron 66:5583
Varma RS, Kumar D (1999) Org Lett 1:697
Zhang X, Jiang X, Zhang K, Mao L, Luo J, Chi C, Chan HSO, Wu J (2010) J Org Chem 75:8069
Ostrowska K, Piegza E, Rapala-Kozik M, Stadnicka K (2012) Eur J Org Chem 2012:3636
Liu RL, Lu H-Y, Li M, Hu S-Z, Chen C-F (2012) RSC Adv 2:4415
Wielopolski M, Marszalek M, Brunetti FG, Joly D, Calbo J, Arago J, Moser JE, Humphry-Baker R, Zakeeruddin SM, Delgado JL, Gratzel M, Orti E, Martin NJ (2016) Mater Chem C 4:3798
Li W, Li X, Liu M, Wang Q (2017) Arch Pharm Chem Life Sci 350:e1700044
Mughal EU, Sadiq A, Murtaza S, Rafique H, Zafar MN, Riaz T, Khan BA, Hameed A, Khan KM (2017) Bioorg Med Chem 25:100
Legnani L, Toma L, Caramella P, Chiacchio MA, Giofre S, Delso I, Tejero T, Merino P (2016) J Org Chem 81:7733
Nair V, Abhilash KG, Suresh E (2006) Tetrahedron Lett 47:9329
Bernardes GJL, Gamblin DP, Davis BG (2006) Angew Chem Int Ed 45:4007
Tokunaga H, Akiba K, Inamoto N (1972) Bull Chem Soc Jpn 45:506
Zhou X, Zeng Y, Liyan C, Wu X, Yoon J (2016) Angew Chem Int Ed 55:4729
Okazaki R, Inoue K, Inamoto N (1981) Bull Chem Soc Jpn 54:3541
Nakayama J, Takahashi K, Watanabe T, Sugihara Y, Ishii A (2000) Tetrahedron Lett 41:8349
Kajjout M, Hebting Y, Albrecht P, Adam P (2012) Chem Biodivers 9:714
Mishiro K, Hu F, Paley WP, Min W, Lambert TH (2016) Eur J Org Chem 2016:1655
Civcir PU, Kurtay G, Sarıkavak K (2017) Struct Chem 28:773
Capperucci A, Degl’Innocenti A, Ricci A, Mordini A, Reginato G (1991) J Org Chem 56:7323
Li GM, Niu S, Segi M, Tanaka K, Nakajima T, Zingaro RA, Reibenspies JH, Hall MB (2000) J Org Chem 65:6601
Umasekhar B, Ganapathi E, Chatterjee T, Ravikanth M (2015) Dalton Trans 44:16516
Kumar SV, Yadav SK, Raghava B, Saraiah B, Ila H, Rangappa KS, Hazra A (2013) J Org Chem 78:4960
Matsuo T, Tamao K (2015) Bull Chem Soc Jpn 88:1201
Pickl M, Swoboda A, Romero E, Winkler CK, Binda C, Mattevi A, Faber K, Fraaije MW (2018) Angew Chem Int Ed 57:2864
Vinayaka AC, Sadashiva MP, Wu X, Biryukov SS, Stoute JA, Rangappa SS, Gowda DC (2014) Org Biomol Chem 12:8555
Yugandar S, Konda S, Parameshwarappa G, Ila H (2016) J Org Chem 81:5606
Goszczycki P, Stadnicka K, Brela M, Grolik J, Ostrowska K (2017) J Mol Struct 1146:337
Raghava B, Parameshwarappa G, Acharya A, Swaroop TR, Rangappa KS, Ila H (2014) Eur J Org Chem 2014:1882
Rombola M, Sumaria CS, Montgomery TD, Rawal VH (2017) J Am Chem Soc 139:5297
Rombola M, Rawal VH (2018) Org Lett 20:514
Ishii A, Ishida T, Kumon N, Fukuda N, Oyama H, Inamoto N, Iwasaki F, Okazaki R (1996) Bull Chem Soc Jpn 69:709
Beak P, Worley JW (1972) J Am Chem Soc 94:597
Dagonneau M, Vialle J (1974) Tetrahedron 30:415
Gosselin P, Masson S, Thuillier A (1978) Tetrahedron Lett 1978:2717
Lin C-E, Richardson SK, Wang W, Wang T, Garvey D (2006) Tetrahedron 62:8410
Bailey WF, Bartelson AL, Wiberg KB (2012) J Am Chem Soc 134:3199
Murai T, Ohashi T, Shibahara F (2011) Chem Lett 40:70
Murai T, Morikawa K, Maruyama T (2013) Chem Eur J 19:13112
Yang Y, Perry IB, Lu G, Liu P, Buchwald SL (2016) Science 353:144
Stocker V, Ghinet A, Leman M, Rigo B, Millet R, Farce A, Desravines D, Dubois J, Waterlot C, Gautret P (2013) RSC Adv 3:3683
Nitti A, Villafiorita-Monteleone F, Pacini A, Botta C, Virgili T, Forni A, Cariati E, Boiocchi M, Pasini D (2017) Faraday Discuss 196:143
van Dijken DJ, Chen J, Stuart MCA, Hou L, Feringa BL (2016) J Am Chem Soc 138:660
Pizzolato SF, Collins BSL, van Leeuwen T, Feringa BL (2017) Chem Eur J 23:6174
Chen C-T, Tsai CC, Tsou P-K, Huang G-T, Yu C-H (2017) Chem Sci 8:524
Cheung KY, Yang S, Miao Q (2017) Org Chem Front 4:699
van Leeuwen T, Pol J, Roke D, Wezenberg SJ, Feringa BL (2017) Org Lett 19:1402
Huang F, Liu Z, Wang Q, Lou J, Yu Z (2017) Org Lett 19:3660
Augustin AU, Busse M, Jones PG, Werz DB (2018) Org Lett 20:820
Yugandar S, Konda S, Ila H (2017) Org Lett 19:1512
Jin R, Liu S, Lan Y (2015) RSC Adv 5:61426
Emamian S (2015) RSC Adv 5:72959
Burkhardta SE, Petrovb VA, Manzoa SM (2016) J Fluorine Chem 191:103
Mlostońa G, Kowalskia MK, Obijalskaa E, Heimgartnerb H (2017) J Fluorine Chem 199:92
Mlostoń G, Pipiak P, Heimgartner H (2016) Beilstein J Org Chem 12:716
Mlostoń G, Grzelak P, Linden A, Heimgartner H (2017) Chem Heterocyclic Compds. 53:518
Petrova VA, Marchionea AA, Dooleya R, Marshall W (2017) J Fluorine Chem 196:7
Hejmanowska J, Jasiński M, Mlostoń G, Albrecht L (2017) Eur J Org Chem 2017:950
Author information
Authors and Affiliations
Corresponding author
Additional information
This article is part of the Topical Collection “Sulfur Chemistry”; edited by Xuefeng Jiang.
Rights and permissions
About this article
Cite this article
Murai, T. The Construction and Application of C=S Bonds. Top Curr Chem (Z) 376, 31 (2018). https://doi.org/10.1007/s41061-018-0209-0
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s41061-018-0209-0