STEREOCHEMISTRY OF FREE-RADICAL ADDITIONS OF METHANOL AND ACETALDEHYDE TO PERFLUORINATED CYCLOALKENES

被引:7
作者
CHAMBERS, RD [1 ]
KELLY, N [1 ]
EMSLEY, JW [1 ]
JONES, WGM [1 ]
机构
[1] ICI LTD,DIV PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND
关键词
D O I
10.1016/S0022-1139(00)85167-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
γ-Ray and peroxide-initiated additions of methanol and acetaldehyde to perfluorocyclo-butene (3), -pentene (4), and -hexene (5) gave mixtures of stereo-isomers in most cases. Stereospecific cis-addition of acetaldehyde to (5) occurs under γ-initiation. A simple 19F n.m.r. method is advanced to distinguish the geometric isomers. © 1978.
引用
收藏
页码:49 / 62
页数:14
相关论文
共 19 条
[1]   RING INVERSION IN FLUORO-CYCLOHEXANES [J].
BURDON, J ;
HOTCHKISS, JC ;
JENNINGS, WB .
TETRAHEDRON, 1977, 33 (14) :1745-1747
[2]  
CHAMBERS RD, 1973, FLUORINE ORGANIC CHE, P173
[3]   BLOCKED CONFORMATIONS IN POLYFLUORINATED SERIES - APPLICATION TO STUDY OF DIASTEREOISOMERISM IN REACTION OF PERFLUORINATED OLEFINS WITH OXYGENATED HETEROCYCLIC-COMPOUNDS [J].
COURTIEU, J ;
JULLIEN, J ;
NGUYENTHOILAI ;
GONORD, P ;
KAN, SK .
TETRAHEDRON, 1976, 32 (06) :669-674
[4]   ELECTRIC FIELDS IN FLUOROCYCLOHEXANES AND MAGNITUDE OF 19F CHEMICAL SHIFTS [J].
EMSLEY, JW .
MOLECULAR PHYSICS, 1965, 9 (04) :381-&
[5]   FLUOROCYCLOHEXANES .3. 1H-4H-2H AND 1H-2H-4H-NONAFLUOROCYCLOHEXANE AND DERIVED COMPOUNDS [J].
GODSELL, JA ;
STACEY, M ;
TATLOW, JC .
TETRAHEDRON, 1958, 2 (3-4) :193-202
[6]   NUCLEAR MAGNETIC RESONANCE SPECTRA OF CYCLIC FLUOROCARBONS .1. 19F SPECTRA OF FLUOROCYCLOHEXANES [J].
HOMER, J ;
THOMAS, LF .
TRANSACTIONS OF THE FARADAY SOCIETY, 1963, 59 (491) :2431-&
[7]   RADICAL-ADDITION OF TOLUENE TO FLUOROCYCLOBUTENES [J].
KIMOTO, H ;
MURAMATSU, H ;
INUKAI, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (10) :2815-2816
[8]  
KUCERA J, 1974, RADIAT RES REV, V5, P93
[9]   THE FREE-RADICAL CATALYZED ADDITION OF ALCOHOLS AND ALDEHYDES TO PERFLUOROOLEFINS [J].
LAZERTE, JD ;
KOSHAR, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (04) :910-914
[10]   CHEMISTRY OF ORGANIC FLUORINE-COMPOUNDS .12. RADICAL-ADDITION OF TRIMETHYLAMINE AND TRIETHYLAMINE TO TRIFLUOROCHLOROETHYLENE [J].
LISKA, F ;
KUBELKA, V .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1972, 37 (04) :1381-&