β-Keto Sulfoxides. II<sup>1,2</sup>

Russell, Glen A.; Sabourin, Edward T.; Mikol, G. J.

doi:10.1021/jo01347a027

Cited by 54 publications

(20 citation statements)

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“…(32). 671 An interesting decomposition of a disulfide (32) bridge by manganese dioxide has been described. Thus, slight warming of bis [trimethylsilyl] disulfide (669) with the reagent at 28°e yielded hexamethyldisiloxane (670) in 25 % yield.…”

Section: Organic Sulfidesmentioning

confidence: 99%

The Oxidation of Organic Compounds by Active Manganese Dioxide

Fatiadi

1986

Organic Syntheses by Oxidation With Metal Compounds

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Section: Organic Sulfidesmentioning

confidence: 99%

The Oxidation of Organic Compounds by Active Manganese Dioxide

Fatiadi

1986

Organic Syntheses by Oxidation With Metal Compounds

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“…90%. 229(210, 228(26), 227(100), 213(1 I), 123(7), 11 1 (12), 110(21), 109(17), 97(27), 96(14), 95(34), 87(88), 83(34), 82(16), 81(36), 69(40), 68(16), 67(32), 61(18), 57(32) -': 3026, 3023,2956, 1632(w), 1602, 1496, 1453, 1419, 1044'H NMR (200 MHz), 6: 7.33-7.15 (m, 5H), 6.50 (dt, J=6.6and 15.5 Hz, lHh6.24 (d, J=15.5Hz,lH),2.79(t,J=7.5,2H),2.55(q,J=ca.7Hz,2H),2.53 (s, 3H); 13c NMR (50.3 MHz),6: 140.32,138.91,134.64,128.33,128.27,126.09,40.55,34.28,33.42;MS (ei),tdz(%): 195(M + 1,13),194(14), 177 (10), 131(42), 130(22), 129(25), 128(13), 115(1 l), 103(19), 92(67), 91(100), 89(12), 88(19), 87(63), 86(75), 84(88), 77(12), 65(31), 63(14); MS (ei, high resolution), d z , calcd. for Cl ,HI4OS: 194.0762;found: 194.0762.…”

Section: -Chloro-3-(methylsuifir~yl)propyl Benzene (1hb)mentioning

confidence: 99%

On the conformational preferences of the dehydrochlorination of α-chlorosulfoxides

Schwan¹,

Roche²,

Gallagher³

et al. 1994

Can. J. Chem.

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Several acyclic a-chlorosulfoxides have been shown to undergo a y-dehydrochlorination upon treatment with LDA. The proposed immediate products of y-dehydrochlorination, thiirane-S-oxides, are unstable under the basic conditions and react further with the LDA; the isolated products are usually E-alkenes and (or) E-vinyl sulfoxides. Some of the proposed intermediate thiirane-S-oxides, compounds 6 , 7 , 8 , and 18, were synthesized independently and treated with one equivalent of LDA in order to mimic the second step of the overall dehydrochlorinatiodring opening sequence. The products obtained from the reactions of compounds 6 and 18 compared favourably with those products which were believed to arise from certain conformations of a-chlorosulfoxides 1kB and le, respectively. The addition of one equivalent of LDA to 1kA afforded a mixture containing thiirane-S-oxide 8, which is proposed as the immediate product of y-dehydrochlorination of 1kA. The configurations of 1kB and 1hA were both shown to be threo by X-ray crystallographic studies. Those conformations which are preferred for the dehydrochlorination possess a geometry where the sulfinyl oxygen is nrlti to any of the substituents of the ring carbons. ADRIAN L. SCHWAN, MICHAEL R. ROCHE, JOHN F. GALLAGHER et GEORGE FERGUSON. Can. J. Chem. 72,312 (1994).On dCmontre que, par traitement avec du LDA, plusieurs a-chlorosulfoxydes subissent une y-dCshydrochloration. Les produits immCdiats proposCs pour cette rkaction, les S-oxydes de thiirane, sont instables dans les conditions basiques de la rCaction et reagissent ti nouveau avec le LDA; les produits isolCs sont habituellement des (IT-alcknes et (ou) des (0-vinylsulfoxydes. On a synthCtisC par des voies independantes quelques-uns des intermkdiaires S-oxydes de thiirane proposCs, les composCs 6 , 7 , 8 et 18, et, dans le but d'Cvaluer leur comportement dans la deuxieme Ctape de la sequence globale de dCshydrochloratiodouverture de cycle, on les a soumis B I'action d'un Cquivalent de LDA. Les produits obtenus lors des rCactions des composCs 6 et 18 se comparent favorablement avec les produits qui devraient &tre obtenus respectivement 2 partir de certaines conformations des a-chlorosulfoxydes 1kB et le. L'addition d'un equivalent de LDA sur le composC 1kA conduit B un melange contenant l'oxyde de thiirane 8 que l'on propose comme intermkdiaire lors de la y-dCshydrochloration du produit 1kA. Faisant appel B des Ctudes cristallographiques par diffraction des rayons X, on a dtterminC que les configurations 1kB et 1hA sont thre'o. Les conformations privilCgiCes pour la dCshydrochloration possedent une gComCtrie dans la quelle l'oxygkne du sulfinyle est arlti par rapport B tous les substituants carbones du cycle.[Traduit par la rCdaction]

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“…The maximum at 309 nm is usually referred to the enol form of the {3-diketone, which is stabilised by intramolecular hydrogen bonding. Nevertheless, this 13keto sulfoxide is able to form a carbanion [3] which can be alkylated [4,5]. Nevertheless, this 13keto sulfoxide is able to form a carbanion [3] which can be alkylated [4,5].…”

mentioning

confidence: 99%