Chemistry of the β-Thiolactones: Substituent and Solvent Effects on Thermal Decomposition and Comparison with the β-Lactones

被引：8

作者：

Noel, Amandine ^{[1
]}

Delpech, Bernard ^{[1
]}

Crich, David ^{[2
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91190 Gif Sur Yvette, France

[2] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 09期

关键词：

PROTEASOME INHIBITORS; NITRIC-OXIDE; DECARBOXYLATION; MECHANISM; SALINOSPORAMIDE; ACID; DIPHENYLKETENE; CYCLOADDITION; PROPIOLACTONE; THERMOLYSIS;

D O I：

10.1021/jo500577c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of di-, tri-, and tetraalkyl beta-thiolactones and beta-lactones is described as well as their thermal decomposition with extrusion of carbon oxysulfide and carbon dioxide in two solvents of opposite polarities. The beta-thiolactones are considerably more thermally stable than the beta-lactones and require higher temperatures for efficient decomposition in both solvents, whatever the degree of substitution. The results are interpreted in terms of a zwitterionic mechanism for fragmentation with a change in the rate-determining step between the two series.

引用

页码：4068 / 4077

页数：10

共 86 条

[1] The standard enthalpies of formation of 1-and 2-Adamantyl cations and radicals.: An ab initio study [J].

Abboud, JLM ;

Castaño, O ;

Dávalos, JZ ;

Gomperts, R .

CHEMICAL PHYSICS LETTERS, 2001, 337 (4-6) :327-330

[2] Solvolysis of (Z)-5-trimethylstannyl 2-adamantyl p-bromobenzenesulfonate:: Mechanistic implications of a record-breaking secondary α-deuterium kinetic isotope effect for an SN1 substrate [J].

Adcock, W ;

Trout, NA ;

Vercoe, D ;

Taylor, DK ;

Shiner, VJ ;

Sorensen, TS .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5399-5402

[3]

[Anonymous], FLUOR EL LIQ FC 71 P

[4] CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES [J].

ARNOLD, LD ;

KALANTAR, TH ;

VEDERAS, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7105-7109

[5] A new structural class of proteasome inhibitors identified by microbial screening using yeast-based assay [J].

Asai, A ;

Tsujita, T ;

Sharma, SV ;

Yamashita, Y ;

Akinaga, S ;

Funakoshi, M ;

Kobayashi, H ;

Mizukami, T .

BIOCHEMICAL PHARMACOLOGY, 2004, 67 (02) :227-234

[6] Belactosin A, a novel antitumor antibiotic acting on cyclin/CDK mediated cell cycle regulation, produced by Streptomyces sp. [J].

Asai, A ;

Hasegawa, A ;

Ochiai, K ;

Yamashita, Y ;

Mizukami, T .

JOURNAL OF ANTIBIOTICS, 2000, 53 (01) :81-83

[7] 1- and 2-adamantyl radicals and cations in the gas phase: Thermochemistry and mass spectrometry [J].

Aubry, C ;

Holmes, JL ;

Walton, JC .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (08) :1389-1393

[8] Synthesis and biological investigation of the β-thiolactone and β-lactam analogs of tetrahydrolipstatin [J].

Aubry, Sylvain ;

Aubert, Genevieve ;

Cresteil, Thierry ;

Crich, David .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (13) :2629-2632

[9] Exploring the potential of the β-thiolactones in bioorganic chemistry [J].

Aubry, Sylvain ;

Sasaki, Kaname ;

Eloy, Laure ;

Aubert, Genevieve ;

Retailleau, Pascal ;

Cresteil, Thierry ;

Crich, David .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) :7134-7143

[10] α,β-unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions:: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor [J].

Balskus, Emily P. ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6810-6812

← 1 2 3 4 5 6 7 8 9 →