1015-49-2

Upstream product

• 20588-68-5 N,N-diethylsulfamoyl chloride 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 1269657-62-6 3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium trifluoromethanesulfonate 
• 109-89-7 diethylamine 
• 1198183-95-7 phenyl 1H-imidazole-1-sulfonate 

Downstream Products

• 30988-93-3 N,N-diethyl-4-hydroxybenzenesulfonamide 
• 858364-68-8 N,N-diethyl 2-pinacolboronatephenyl O-sulfamate 
• 644-08-6 4-Methylbiphenyl 
• 858364-65-5 N,N-diethyl 2-bromophenyl O-sulfamate 
• 858364-66-6 N,N-diethyl 2-iodophenyl O-sulfamate 
• 635-90-5 1-phenylpyrrole 
• 27331-43-7 1-(3-methoxybiphenyl)naphthalene 
• 605-02-7 1-phenylnaphthalene 
• 90-15-3 α-naphthol 
• 858364-69-9 N,N-diethyl 2-bromo-6-trimethylsilylphenyl O-sulfamate 
• 858364-70-2 N,N-diethyl 2-bromo-6-methoxyphenyl O-sulfamate 
• 858364-62-2 N,N-diethyl 2-trimethylsilylphenyl O-sulfamate 

Relevant academic research and scientific papers

O-(Aminosulfonylation) of phenols and an example of slow hydrolytic release

Sequential replacement of imidazole from sulfonyldiimidazole by phenols and then amines leads to O-arylsulfamate esters. Application of this coupling method to 19 phenols and 6 amines generates a library of 114 sulfamate esters, Ar-OSO2-NR2. A sulfamate based conjugate of ethinyl estradiol was prepared by using the steroid 3-hydroxyl as the phenol component, and an amino amide derived from linoleic acid as the amine. Hydrolysis of this conjugate was studied in aqueous buffer at pH values 2, 5, and 7.4, and (essentially identical) respective half-lives of 6.8, 6.6, and 6.7 days were observed.

Directed ortho metalation methodology. The N,N-dialkyl aryl O-sulfamate as a new directed metalation group and cross-coupling partner for grignard reagents

(Chemical Equation Presented) The ortho metalation (RLi/THF/-93°C) of 3 followed by quench with a variety of electrophiles constitutes a new general route to substituted aryl O-sulfamates 4a-k. The Kumada-Corriu cross-coupling of O-sulfamates 4e, 4n-s, and 6a with Grignard reagents gives biaryls 9a-m, and the use of 2-halo and boron derivatives 4h, 4i, and 4k for Suzuki-Miyaura cross-coupling and generation of benzynes leads to naphthols 7a and 7b. A relative metalation ranking of the OSONEt2 is reported.

Versatile Synthesis of Sulphamate Esters by Phase-transfer Methods

The syntheses of sulphamate esters of the general types R1R2NSO3R3, RNHSO3R3, and H2NSO3R3, where R3 may be aliphatic or aromatic, have been achieved in good yield by reaction of the appropriate sulphamoyl chlorides with alcohols and phenols under mild phase-transfer conditions.The present methods have led to generally higher yields, and to shorter reaction times and lower reaction temperatures than were hitherto found necessary.The prior preparation of the alkoxide has also been obviated.Some esters have been rearranged to the isomeric betaines.