138665-17-5Relevant academic research and scientific papers
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.
