83040-02-2Relevant academic research and scientific papers
Sulfination of alcohols with sodium sulfinates promoted by BF3·OEt2: An unexpected access
Huang, Mingming,Hu, Liangzhen,Shen, Hang,Liu, Qing,Hussain, Muhammad Ijaz,Pan, Jing,Xiong, Yan
supporting information, p. 1874 - 1879 (2016/04/19)
A BF3·OEt2-promoted direct substitution of various alcohols with sodium sulfinates affording sulfinates under mild conditions has been developed. Further reaction of the hydroxysteroids achieves the highly complex sulfinates in good yields, which are two potential pharmacophores routinely encountered in drug discovery.
An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions
Hajipour, Abdol R.,Falahati, Ali R.,Ruoho, Arnold E.
, p. 2717 - 2719 (2007/10/03)
The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N′-dicyclohexylcarbodiimide (DCC) under solvent-free conditions.
O-sulfinylation with methanesulfonyl cyanide or p-toluenesulfonyl cyanide and DBU
Barton,Jaszberenyi,Theodorakis
, p. 2585 - 2588 (2007/10/02)
Reaction of methanesulfonyl cyanide or p-toluenesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates is suggested.
O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide
Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.
, p. 9167 - 9178 (2007/10/02)
Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]under-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.
SULFINIC ACIDS AND RELATED COMPOUNDS. 21. PREPARATION OF CRYSTALLINE SULFINIC ESTERS
Lee, Chew,Field, Lamar
, p. 35 - 46 (2007/10/02)
In a search for means of preparing stable crystalline esters of sulfinic acids, yields from p-toluenesulfinic acid as a model were 53-92 percent with 1,1'-carbonyldiimidazole (CDI, 2) as a coupling reagent for a variety of alcohols.The best coupling reagents were CDI and chlorotrimethylsilane (16).The agent 16 could be used with sulfinate salts, as could CDI with in situ acidification.The best alcohols were 1-adamantanol and p-nitrobenzyl alcohol.Among alkanesulfinic esters, methanesulfinates were unstable oils obtainable only in low yields, but 1-butanesulfinates were obtained in 52-56 percent yield (although still as oils).As a stable disulfinic acid, 1,4-butanedisulfinic acid gave a nicely crystalline di-1-adamantyl ester (mp 123-125 deg C), but another alkanedisulfinate salt or acid that contained a disulfide moiety gave no diester by use either of 2 or 16.Key words: 1,1'-Carbonyldiimidazole, chlorotrimethylsilane, sulfinic acids, sulfinic acid esters, sulfinic acid salts, p-toluenesulfinic acid.
