- A mild method for conversion of alcohols to dialkyl sulfites by use of Na2SO3/SOCl2
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Alcohols are easily converted to their corresponding dialkyl sulfite under mild reaction conditions using Na2SO3/SOCl2 in moderate to good isolated yields.
- Kiasat, Ali Reza,Kazemi, Foad,Khosravian, Froogh
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p. 427 - 431
(2007/10/03)
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- Reactions of N-sulfinylfluoroalkanesulfonyl amines with nucleophiles containing reactive hydrogen
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The reactions of N-sulfinylfluoroalkanesulfonyl amines, RfSO2NSO (1), with malonate or dialkyl phosphite gave 1:1 adducts RfSO2NHS(O)Nu , and with alcohols or phenols formed RfSO2NH2 and the sulfites O=S(OR)2 by double addition .Trans-sulfinylation occurred during the reaction of 1 with anilines (C6H5NH2, 4-FC6H4NH2 and C6F5NH2).
- Li, Ai-Wen,Xu, Bin,Wang, Chao-Xian,Zhu, Shi-Zheng
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- Conversion of Some Pyrimidine 2'-Deoxyribonucleosides into the Corresponding 2',3'-Didehydro-2',3'-dideoxynucleosides
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Thymidine 4b was converted into 2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine 7b in ca. 65percent isolated yield by being heated at 155 deg C with an excess of diphenyl sulfite and 1-methylimidazole in N,N-dimethylacetamide solution. 2'-Deoxyuridine 4a, 2'-deoxy-5-ethyluridine 4c and 2'-deoxy-5-fluorouridine 4d were similarly converted into 2,3'-anhydronucleosides which were isolated as their 5'-O-(tert-butyldimethylsilyl) derivatives 8a, 8c and 8d in 51, 50 and 59percent yield, respectively.When the oxetane derivatives 5a-d, prepared by the literature procedure from the parent 2'-deoxynucleosides 4a-d, were heated with an excess of sodium hydride in N,N-dimethylacetamide solution at 100 deg C, they were converted into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6a-d in 68, 76, 69 and 74percent isolated yield, respectively.The latter compounds were similarly prepared from the 2,3'-anhydronucleosides 7a-d in 71, 81, 69 and 74percent isolated yield, respectively. 2,3'-Anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-(trifluoromethyl)- and -5-iodo-1-(β-D-threo-pentofuranosyl)uracil 8e and 8f, which were themselves prepared from the parent 2'-deoxynucleosides 4e and 4f, respectively, in ca. 60 and 50percent yield, were converted by a three-step procedure via the intermediate 2'-deoxy-3'-(phenylseleno) derivatives 10e and 10f into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6e and 6f in 52 and 49percent overall yield, respectively.Compound 8e was also converted into 2',3'-dideoxy-5-(trifluoromethyl)uridine 11b and 3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine 11c in 49 and 66percent overall yield, respectively.
- Joshi, Bhalchandra V.,Rao, T. Sudhakar,Reese, Colin B.
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p. 2537 - 2544
(2007/10/02)
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