Rates of C-S bond cleavage in tert-alkyl phenyl sulfide radical cations

被引：31

作者：

Baciocchi, E

Del Giacco, T

Gerini, MF

Lanzalunga, O

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[2] CNR, IMC, Sez Meccanismi Reaz, I-00185 Rome, Italy

[3] Univ Perugia, Dipartimento Chim, I-06123 Perugia, Italy

[4] Univ Perugia, CEMIN, I-06123 Perugia, Italy

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 04期

关键词：

D O I：

10.1021/ol052834y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical cations of tert-alkyl phenyl sulfides 1-4 have been generated photochemically in MeCN in the presence of the N-methoxyphenanthridinium cation (MeOP+), and the rates of C-S bond cleavage have been determined by laser flash photolysis.

引用

页码：641 / 644

页数：4

共 35 条

[1] Influence of carbocation stability in the gas phase on solvolytic reactivity: beyond bridgehead derivatives [J].

Abboud, JLM ;

Alkorta, I ;

Davalos, JZ ;

Müller, P ;

Quintanilla, E ;

Rossier, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :3786-3796

[2] Photochemical electron-transfer reactions between sulfides and tetranitromethane.: Oxidation vs fragmentation of the sulfide radical-cation intermediate [J].

Adam, W ;

Argüello, JE ;

Peñéñory, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3905-3910

[3] STABILITIES OF CARBOCATIONS IN SOLUTION .14. AN EXTENDED THERMOCHEMICAL SCALE OF CARBOCATION STABILITIES IN A COMMON SUPERACID [J].

ARNETT, EM ;

HOFELICH, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2889-2895

[4] MEDIUM AND STRUCTURE EFFECTS ON THE ANODIC-OXIDATION OF ARYL ARYLMETHYL SULFIDES [J].

BACIOCCHI, E ;

ROL, C ;

SCAMOSCI, E ;

SEBASTIANI, GV .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5498-5502

[5] Steady-state and laser flash photolysis study of the carbon-carbon bond fragmentation reactions of 2-arylsulfanyl alcohol radical cations [J].

Baciocchi, E ;

Del Giacco, T ;

Elisei, F ;

Gerini, MF ;

Lapi, A ;

Liberali, P ;

Uzzoli, B .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8323-8330

[6] Rotational barriers, charges, and spin densities in alkyl aryl sulfide radical cations: A density functional study [J].

Baciocchi, E ;

Gerini, MF .

JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (12) :2332-2338

[7] FRAGMENTATION REACTIONS OF AROMATIC CATION RADICALS - A TOOL FOR THE DETECTION OF ELECTRON-TRANSFER MECHANISMS IN BIOMIMETIC AND ENZYMATIC OXIDATIONS [J].

BACIOCCHI, E .

XENOBIOTICA, 1995, 25 (07) :653-666

[8] STEREOCHEMISTRY OF THE C-S BOND-CLEAVAGE IN 1-PHENYLETHYL PHENYL SULFIDE RADICAL-CATION - EVIDENCE FOR A UNIMOLECULAR PATHWAY [J].

BACIOCCHI, E ;

FASELLA, E ;

LANZALUNGA, O ;

MATTIOLI, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1071-1073

[9] Mechanistic aspects of β-bond-cleavage reactions of aromatic radical cations [J].

Baciocchi, E ;

Bietti, M ;

Lanzalunga, O .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (04) :243-251

[10] THE MECHANISM OF ENZYMATIC AND BIOMIMETIC OXIDATIONS OF AROMATIC SULFIDES AND SULFOXIDES [J].

BACIOCCHI, E ;

LANZALUNGA, O ;

MARCONI, F .

TETRAHEDRON LETTERS, 1994, 35 (52) :9771-9774

← 1 2 3 4 →