60091-81-8Relevant academic research and scientific papers
One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride
Dubois, Rudy,Epifanov, Maxim,Hodgson, Jack W.,Mo, Jia Yi,Sammis, Glenn M.
supporting information, p. 4958 - 4962 (2020/04/22)
The Mitsunobu reaction is a powerful transformation for the one-pot activation and substitution of aliphatic alcohols. Significant efforts have focused on modifying the classic conditions to overcome problems associated with purification from phosphine-based byproducts. Herein, we report a phosphine free method for alcohol activation and substitution that is mediated by sulfuryl fluoride. This new method is effective for a wide range of primary alcohols using phthalimide, di-tert-butyl-iminodicarboxylate, and aromatic thiol nucleophiles in 74 % average yield. Activated carbon nucleophiles and a deactivated phenol were also effective for this reaction in good yields. Secondary alcohols were also successful substrates using aryl thiols, affording the corresponding sulfides in 56 % average yield with enantiomeric ratios up to 99:1. This new protocol has a distinct synthetic advantage over many existing phosphine-based methods as the byproducts are readily separable. This feature was exploited in several examples that did not require chromatography for purification. Furthermore, the mild reaction conditions enabled further in situ derivatization for the one-pot conversion of alcohols to amines or sulfones. This method also provides a boarder nucleophile scope compared to existing phosphine-free methods.
An Iodine-Mediated Hofmann-L?ffler-Freytag Reaction of Sulfoximines Leading to Dihydroisothiazole Oxides
Zhang, Duo,Wang, Han,Cheng, Hanchao,Hernández, José G.,Bolm, Carsten
supporting information, p. 4274 - 4277 (2017/10/23)
A Hofmann-L?ffler-Freytag type cyclization reaction of S-aryl-S-phenylpropyl sulfoximines (and related derivatives) was developed. Using molecular iodine as the initiator under visible light a series of five-membered cyclic products was obtained in moderate to high yields. The approach represents a new strategy for the synthesis of dihydroisothiazole oxides and benzo[d]isothiazoles-1-oxides. (Figure presented.).
A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation
Mukaiyama, Teruaki,Ikegai, Kazuhiro
, p. 1522 - 1523 (2007/10/03)
A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation was established. Various primary, secondary, and tertiary alcohols were successfully converted into the corresponding su
Arylisothiocyanate for the regulation of plant growth
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, (2008/06/13)
New arylisothiocyanates corresponding to the formula STR1 wherein R represents alkyl, alkoxy or halogen X represents oxygen or sulfur and P represents an integer of from 2 to 5 are disclosed. They can be used for the regulation of plant growth especially for the dessication and defoliation of unlignified parts of plants above the soil.
