OZONOLYSIS OF DEUTERIUM-LABELED 1-OLEFINS

被引：11

作者：

MURRAY, RW

WILLIAMS, GJ

机构：

[1] Bell Telephone Laboratories, Inc., Murray Hill

[2] Chemistry Department, University of Adelaide, Adelaide

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 06期

关键词：

D O I：

10.1021/jo01258a081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ozonolysis of either cis- or trans-1-deuteriohexene-1 gives a 50/50 mixture of cis- and trans-1-deuteriohexene-1 ozonide. Ozonolysis of 1,1-dideuteriohexene-1 in the presence of a fivefold excess of formaldehyde leads to only 39% incorporation of the formaldehyde in the hexene-1 ozonide. Ozonolysis of an equimolar mixture of 1,1-dideuteriohexene-l and heptene-1 leads to hexene-1 and heptene-1 ozonides containing 80.3 and 27% dideuterio ozonide, respectively. © 1969, American Chemical Society. All rights reserved.

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页码：1896 / &

相关论文

共 16 条

[1] COMPETITION BETWEEN COMPLETE AND PARTIAL CLEAVAGE DURING OZONATION OF OLEFINS [J].

BAILEY, PS ;

LANE, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4473-&

[2] HIGHLY BRANCHED MOLECULES .4. SOLVOLYSIS OF THE PARA-NITROBENZOATE OF TRI-TERT-BUTYLCARBINOL AND SOME OF ITS HOMOLOGS [J].

BARTLETT, PD ;

STILES, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (10) :2806-2814

[3] STEREOSPECIFICITY IN OZONIDE AND CROSS-OZONIDE FORMATION [J].

BAULD, NL ;

THOMPSON, JA ;

HUDSON, CE ;

BAILEY, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (07) :1822-&

[4]

BIBLE RH, 1965, INTERPRETATION NMR S, P61

[5] THE HYDROBORATION OF ACETYLENES - A CONVENIENT CONVERSION OF INTERNAL ACETYLENES TO CIS OLEFINS OF HIGH PURITY AND OF TERMINAL ACETYLENES TO ALDEHYDES [J].

BROWN, HC ;

ZWEIFEL, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (06) :1512-1512

[6] HYDROBORATION .11. HYDROBORATION OF ACETYLENES - A CONVENIENT CONVERSION OF INTERNAL ACETYLENES INTO CIS-OLEFINS AND OF TERMINAL ACETYLENES INTO ALDEHYDES [J].

BROWN, HC ;

ZWEIFEL, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (18) :3834-&

[7]

COOKSOM RC, 1966, TETRAHEDRON S, P355

[8]

Criegee R., 1957, REC CHEM PROGR, V18, P111

[9]

Criegee R, 1959, ACS ADV CHEM SERIES, P133

[10] OZONOLYSIS .10. MOLOZONIDE AS AN INTERMEDIATE IN OZONOLYSIS OF CIS AND TRANS ALKENES [J].

DURHAM, LJ ;

GREENWOOD, FL .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1629-+