Sulfurierungen XI. Über den Mechanismus der Piria-Reaktion

Vrba, Z.; Allan, Z. J.

doi:10.1135/cccc19680431

Cited by 5 publications

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“…A rather interesting preparation of a sulfamate ester was carried out by Weinstein and Chang416 who prepared methyl ferf-butylsulfamate (111) by treating A/.A/'-di-fert-butylsulfamide with 3 equiv of ferf-butyl hypochlorite. A mechanism is proposed which involves an intermediate /V-sulfonyl-fert-butylamine (112). The scope of this reaction as a route to sulfamate esters has not been explored.…”

Section: Synthesismentioning

confidence: 99%

“…An efficient method for the conversion of tertiary alcohols 0SO2C! + HN = SO(Me)2 C5H5N n>NS02NS0(Me)2 161 (112) to amines5465 involves reaction of the alcohol with chlorosulfonyi isocyanate to give A/-chlorosulfonylurethanes which decompose to give the sulfamyl chloride of the alcohol. These are best reduced to amines by formation of the ferf-butoxycarbonylhydrazides and reduction with Pb(OAc)4.…”

Section: Physical Studiesmentioning

confidence: 99%

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Sulfamic acid and its N-substituted derivatives

Benson¹,

Spillane²

1980

Chem. Rev.

113

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Section: Synthesismentioning

confidence: 99%

Section: Physical Studiesmentioning

confidence: 99%

Sulfamic acid and its N-substituted derivatives

Benson¹,

Spillane²

1980

Chem. Rev.

113

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“…sulfuric acid and the rearrangement of phenylsulfamic acid 19 and in the reduction of nitro compounds with sulfite (Piria reaction). 20 Disulfamates could, since they contain a sulfamate moiety, be sweet compounds and this indicates another possible use.…”

mentioning

confidence: 99%

Synthesis and tastant properties of disulfamates. Multisulfamation studies

Spillane

Ryder

Concagh

et al. 2001

J. Chem. Soc., Perkin Trans. 2

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Twenty four disulfamates, one trisulfamate, two tetrasulfamates and two monosulfamates have been made. The disulfamates are of two types: RN(SO 3 Na) 2 (Type A, compounds 1-20) and NaO 3 S(H)NRЈN(H)SO 3 Na (Type B, compounds 21-24) and all except three (which had not been tasted) are new materials. The positions of the -SO 3 Na groups in compounds 21-23 have been established by the use of model compounds (e.g. parent amines, appropriate monosulfamates) and 13 C-NMR. Some multisulfamation synthesis leading to compounds 25-27 has been carried out. Taste data have been obtained for almost all the sulfamates made and the significance of these in relation to structure-taste studies for sulfamate sweeteners is discussed. In particular, the possibility that the entity CHN(R)SO 3 Ϫ might function as a hydrogen source in the Shallenberger-Acree, multicomponent attachment and α-helical protein receptor mechanisms has been examined.

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Piria Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction is a two‐step preparation of aromatic amines and amino sulfonic acids by the reduction of aromatic nitro compounds with bisulfite followed by hydrolysis in mineral acid and is generally known as the Piria reaction. All mechanistic features of the reaction have been presented and it has been found that in 4‐nitrophenol, the sulfonic group enters the meta ‐position of the nitro group. In addition, it has been found that sodium sulfite and the partially neutralized NaHSO 3 are very effective in this reaction. This reaction has been applied for the preparation of aromatic amines.

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Sulfurierungen XI. Über den Mechanismus der Piria-Reaktion

Cited by 5 publications

References 0 publications

Sulfamic acid and its N-substituted derivatives

Sulfamic acid and its N-substituted derivatives

Synthesis and tastant properties of disulfamates. Multisulfamation studies

Piria Reaction

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