NEGATIVE HYPERCONJUGATION DOES NOT PLAY AN IMPORTANT ROLE IN ALPHA-FLUORO SULFIDES - AN EXPERIMENTAL DEMONSTRATION

被引：11

作者：

FUJITA, M ^{[1
]}

SUZUKI, M ^{[1
]}

OGATA, K ^{[1
]}

OGURA, K ^{[1
]}

机构：

[1] CHIBA UNIV,CTR CHEM ANAL,CHIBA 260,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 11期

关键词：

D O I：

10.1016/0040-4039(91)80359-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic oxidation of alpha-fluoro sulfides preferentially proceeded via anti attack of the oxidant to the C-F bond. This result is inconsistent with the significant stereoelectronic effect based on sigma-C-F* - n(S) interaction (negative hyperconjugation), which should otherwise make the anti attack unfavorable. Theoretical support is also disclosed.

引用

页码：1463 / 1466

页数：4

共 18 条

[1] BINKLEY JS, QCPE437 PROGR
[2] STRUCTURES AND STABILITIES OF FLUORINATED CARBANIONS - EVIDENCE FOR ANIONIC HYPERCONJUGATION
DIXON, DA
FUKUNAGA, T
SMART, BE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (14) : 4027 - 4031
[3] CRYSTAL AND MOLECULAR-STRUCTURE OF [(CH3)2N]3S+CF3O- - EVIDENCE FOR NEGATIVE FLUORINE HYPERCONJUGATION
FARNHAM, WB
SMART, BE
MIDDLETON, WJ
CALABRESE, JC
DIXON, DA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) : 4565 - 4567
[4] Fukui K., 1975, THEORY ORIENTATION S
[5] Hirsch J. A., 1967, TOP STEREOCHEM, V3, P199, DOI [10.1002/9780470147108.ch4, DOI 10.1002/9780470147108.CH4]
[6] CH3 AND CF3 HYPERCONJUGATION IN THE 2ND ROW
MAGNUSSON, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (01) : 11 - 16
[7] MOLECULAR-STRUCTURE AND VIBRATIONAL-SPECTRUM OF P(CF3)3 - POSSIBLE EXAMPLE OF AN ALTRUISTIC COVALENT INTERACTION
MARSDEN, CJ
BARTELL, LS
[J]. INORGANIC CHEMISTRY, 1976, 15 (11) : 2713 - 2717
[8] (DIETHYLAMINO)SULFUR TRIFLUORIDE IN ORGANIC-SYNTHESIS .2. THE TRANSFORMATION OF SULFOXIDES TO ALPHA-FLUORO THIOETHERS
MCCARTHY, JR
PEET, NP
LETOURNEAU, ME
INBASEKARAN, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (03) : 735 - 737
[9] PRETSCH E, 1981, TABELLEN STRUKTURAUF, pH355
[10] NEGATIVE HYPERCONJUGATION - THE ROTATION INVERSION BARRIER IN ALPHA-FLUORAMINES
RAHMAN, MM
LEMAL, DM
DAILEY, WP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) : 1964 - 1966

← 1 2 →