Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 23
623
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Convenient Route to Thiocarbonates from Alcohols, Thiols, and Triphosgene

&
Pages 3467-3471 | Received 03 Jun 2009, Published online: 05 Nov 2010

REFERENCES

  • Wuts , P. G. M. ; Greene , T. W. Greene's Protective Groups in Organic Synthesis, ed. , 4th ; Wiley : Hoboken , NJ , 2007 ; pp. 706 – 771 .
  • (a) Harusawa , S. ; Kurihara , T. [3,3]-Sigmatropic rearrangement of cyclic thionocarbonates of medium ring size . Rev. Heteroatom. Chem. 1997 , 16 , 137 – 169 ; (b) Harusawa , S. ; Kurihara , T. [3,3]-Sigmatropic ring expansion of cyclic thionocarbonates of medium ring size . J. Synth. Org. Chem. Jpn. 1995 , 53 , 712 – 723 .
  • (a) Harusawa , S. ; Osaki , H. ; Fujii , H. ; Yoneda , R. ; Kurihara , T. [3,3]-Sigmatropic ring expansion of cyclic thionocarbonates, 8: Highly stereoselective synthesis of (Z- or E-)-double bonds by controlling chair-like–boat-like transition states in the [3,3]-sigmatropic rearrangement of eight-membered thionocarbonates. Tetrahedron 1992, 48, 9433–9450; (b) Harusawa , S. ; Takemura , S. ; Osaki , H. ; Yoneda , R. ; Kurihara , T. [3,3]-Sigmatropic ring expansion of cyclic thionocarbonates, 9: Total synthesis of (±)-yellow scale pheromone via 10-membered thiolcarbonate. Tetrahedron 1993, 49, 7657–7666; (c) Furlan , R. L. E. ; Mata , E. G. Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives. Arkivok 2003, 32–40; (d) Laak , K. V. ; Scharf , H. D. Synthesis of methyl 2,6-dideoxy-4-thio-α-D-ribohexopyranoxide, a new thio sugar found in calichemicins. Tetrahedron Lett. 1989, 30, 4505–4506; (e) Jones , F. N. Base-catalyzed conversion of thiolcarbonate esters into sulfides: Reactions of xanthate esters. J. Org. Chem. 1968, 33, 4290–4292.
  • Minagawa , M. ; Nakahara , Y. ; Kitsukawa , K. Thiolcarbonate ester stabilizers. U.S. Patent 4199495, 1980 .
  • (a) Bafford , R. A. ; Mageli , O. L. Peroxy thiolcarbonates. Brit. Patent GB 1171324, 1980 ; (b) Bafford , R. A. ; Mageli , O. L. Peroxy thiolcarbonates. U.S. Patent 3478080, 1969 .
  • Dyer , E. ; Bender , H. S. Derivatives of purinethiols: Purine thiolcarbonates and related compounds . J. Med. Chem. 1964 , 7 , 10 – 14 .
  • (a) Newton , B. N. Iodinated thiolcarbonates and method for use as radiographic contrast agents. U.S. Patent 4125554, 1978 ; (b) Movassagh , B. ; Tavoosi , M. Synthesis of S-aryl/alkyl thiolcarbonates from disulfides and chloroformates in the presence of the Zn/AlCl3 system . Monatsh. Chem. 2008 , 139 , 251 – 253 .
  • (a) Pinazzi , C. P. ; Esnault , J. ; Pleurdeau , S. Synthesis of polymers with carbonate–alcohol functional end groups . Eur. Poly. J. 1980 , 16 , 283 – 287 ; (b) Overberger , C. G. ; Ringsdorf , H. ; Weinshenker , N. Preparation and polymerization of S-, O-, and N-vinyl derivatives of carbonic acid: Unsaturated carbonic acid derivatives II . J. Org. Chem. 1962 , 27 , 4331 – 4337 ; (c) Overberger , C. G. ; Daly , W. H. S-Vinyl-O-t-butyl thiolcarbonate: A new route to polymercaptans . J. Am. Chem. Soc. 1964 , 86 , 3402 – 3403 .
  • Grisley , D. W. Methods for preparing S-alkyl-O-aryl thiolcarbonates. U.S. Patent 3151145, 1964 .
  • Bratt , M. O. ; Taylor , P. C. Synthesis of carbonates and related compounds from carbon dioxide via methanesulfonyl carbonates . J. Org. Chem. 2003 , 68 , 5439 – 5444 .
  • Gilligan , W. H. ; Stafford , S. L. O-Chlorocarbonylation of β-nitroalcohols and 2,2,2-trihaloethanols via O-alkyl-S-ethyl thiocarbonates . Synthesis 1979 , 600 – 602 .
  • Bean , M. ; Kohn , H. Studies on the reaction of mitomycin C with potassium ethyl monothiocarbonate under reductive conditions . J. Org. Chem. 1983 , 48 , 5033 – 5041 .
  • Al-Kazimi , H. R. ; Tarbell , D. S. ; Plant , D. A study of the Schönberg rearrangement of diaryl thioncarbonates to diaryl thiolcarbonates . J. Chem. Soc. 1955 , 77 , 2479 – 2482 .
  • Chanyshev , N. T. ; Kalashnikov , S. M. ; Kuramshin , E. M. ; Naimushin , A. I. ; Imashev , U. B. Reaction of potassium phenoxide with carbon oxysulfide in the DMSO-1,4-dioxane system: Synthesis of O-aryl-S-alkylthiocarbonates . Zh. Obshch. Khim. 1990 , 60 , 2568 – 2576 ; Chem. Abstr. 1991, 115, 28833r .
  • Olofson , R. A. ; Cuomo , J. Useful route to alkenyl S-phenyl thiocarbonates: Reagents for the introduction of the enyloxycarbonyl moiety in synthesis . J. Org. Chem. 1980 , 45 , 2538 – 2541 .
  • Mizuno , T. ; Nishiguchi , I. ; Hirashima , T. ; Ogawa , A. ; Kambe , N. ; Sonoda , N. A new selenium-catalyzed synthesis of S-alkyl carbonothioates from alcohols, carbon monoxide, sulfur, and alkyl halides . Tetrahedron Lett. 1990 , 31 , 4773 – 4776 .
  • Mizuno , T. ; Nishiguchi , I. ; Hirashima , T. Sulfur-assisted O-carbonylation of alcohols with carbon monoxide in the presence of DBU . Tetrahedron Lett. 1988 , 29 , 4767 – 4768 .
  • Nishiyama , Y. ; Maehira , K. ; Nakase , J. ; Sonoda , N. A new method for synthesis of S-aryl-O-alkyl thiolcarbonates: Selenium-catalyzed reaction of alcohols with carbon monoxide and diaryl disulfides . Tetrahedron Lett. 2005 , 46 , 7415 – 7417 .
  • (a) Cotarca , L. ; Delogu , P. ; Nardelli , A. ; Šunjić , V. Bis(trichloromethyl)carbonate in organic synthesis . Synthesis 1996 , 553 – 576 ; (b) Eckert , H. ; Forster , B. Triphosgene, a crystalline phosgene substitute . Angew. Chem., Int. Ed. Engl. 1987 , 26 , 894 – 895 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.