On the triggering of free radical reactivity of dimethyldioxirane

被引：46

作者：

Curci, R

Dinoi, A

Fusco, C

Lillo, MA

机构：

[1] Centre CNR M.I.S.O., Dipartimento di Chimica, Università di Bari, I-70126 Bari

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 02期

关键词：

D O I：

10.1016/0040-4039(95)02140-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Performing the reaction in the presence of CCl3Br, and/or in inert gas atmosphere, dramatically changes the reaction kinetics, rate-law and product distribution of adamantane oxyfunctionalization by dimethyldioxirane (la). The kinetics of decomposition of the dioxirane is also markedly influenced by the addition of CCl3Br and by depletion of O-2 gas. ?he data suggest that these conditions can trigger dioxirane radical reactions; these are widely different from the straightforward, highly selective concerted O-insertion into C-H bonds which would take place in the absence of CCl3Br and of conditions inducing radical reactivity.

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页码：249 / 252

页数：4

相关论文

共 18 条

[1] THERMALLY AND PHOTOCHEMICALLY INITIATED RADICAL CHAIN DECOMPOSITION OF KETONE-FREE METHYL(TRIFLUOROMETHYL)DIOXIRANE [J].

ADAM, W ;

CURCI, R ;

NUNEZ, MEG ;

MELLO, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7654-7658

[2] OXYGEN ATOM INSERTION INTO THE BENZYLIC CARBON HYDROGEN-BOND OF (R)-(-)-2-PHENYLBUTANE BY METHYL(TRIFLUOROMETHYL)DIOXIRANE - AN EFFICIENT AND MILD REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (S)-(-)-2-PHENYL-2-BUTANOL [J].

ADAM, W ;

ASENSIO, G ;

CURCI, R ;

GONZALEZNUNEZ, ME ;

MELLO, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :953-955

[3]

ADAM W, 1992, J AM CHEM SOC, V114, P7654

[4] INDUCED HOMOLYSIS OF DIMETHYLDIOXIRANE BY ALKANES AND ALKYL RADICALS IN OXIDATION PROCESSES - THE DRAMATIC ROLE OF MOLECULAR-OXYGEN AND RADICAL INHIBITORS [J].

BRAVO, A ;

FONTANA, F ;

FRONZA, G ;

MELE, A ;

MINISCI, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (15) :1573-1574

[5] KINETICS AND MECHANISMS OF ALKYL ETHER OXIDATION BY PEROXYDISULFATE ION [J].

CURCI, R ;

DELANO, G ;

DIFURIA, F ;

EDWARDS, JO ;

GALLOPO, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (20) :3020-3025

[6] DIOXIRANE OXIDATIONS - TAMING THE REACTIVITY-SELECTIVITY PRINCIPLE [J].

CURCI, R ;

DINOI, A ;

RUBINO, MF .

PURE AND APPLIED CHEMISTRY, 1995, 67 (05) :811-822

[7] RATE LAW FOR OXIDATION OF METHANOL AND ETHANOL BY PEROXYDISULFATE ION [J].

EDWARDS, JO ;

GALLOPO, AR ;

MCISAAC, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (16) :3891-&

[8]

HAMILTON GA, 1974, MOL MECHANISMS OXYGE, pCH10

[9]

Hill C. L., 1988, ADV OXYGENATED PROCE, V1, P1

[10] THERMAL-DECOMPOSITION OF DIMETHYLDIOXIRANE [J].

HULL, LA ;

BUDHAI, L .

TETRAHEDRON LETTERS, 1993, 34 (32) :5039-5042