ONE-POT, ONE-CARBON AND MULTICARBON HOMOLOGATION OF ALKYL-HALIDES - REACTION OF GRIGNARD-REAGENTS WITH CHLOROIODOMETHANE

被引：29

作者：

HAHN, RC ^{[1
]}

TOMPKINS, J ^{[1
]}

机构：

[1] SUNY SYRACUSE,COLL HLTH RELATED PROFESS,HLTH SCI CTR,DEPT LIBERAL ARTS & SCI,SYRACUSE,NY 13210

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)94397-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of a Grignard reagent (RMgX) with chloroiodomethane affords the corresponding iodide (RI) and, depending on R, solvent, and temperature, iodides which are one-carbon and multicarbon homologs of RX. Allyl iodide but not allyl bromide can be monohomologated by the combined action of chloroiodomethane and isopropyl Grignard. © 1990.

引用

页码：937 / 940

页数：4

共 23 条

[1] REACTIONS OF CARBALKOXYCARBENES WITH ALLYL HALIDES . HALONIUM YLIDE INTERMEDIATES [J].

ANDO, W ;

KONDO, S ;

MIGATA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (23) :6516-&

[2] FACILE ONE-POT TRANSFORMATION OF CARBOXYLIC-ACID CHLORIDES INTO 2-SUBSTITUTED ALLYL ALCOHOLS OR EPICHLOROHYDRINS [J].

BARLUENGA, J ;

FERNANDEZSIMON, JL ;

CONCELLON, JM ;

YUS, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :77-80

[3] ORGANOBORANES .46. NEW PROCEDURES FOR THE HOMOLOGATION OF BORONIC ESTERS - A CRITICAL-EXAMINATION OF THE AVAILABLE PROCEDURES TO ACHIEVE CONVENIENT HOMOLOGATION OF BORONIC ESTERS [J].

BROWN, HC ;

SINGH, SM ;

RANGAISHENVI, MV .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3150-3155

[4] SYNTHETIC STUDIES ON 2R,4',8'R-ALPHA-TOCOPHEROL - APPROACH UTILIZING SIDE-CHAIN SYNTHONS OF MICROBIOLOGICAL ORIGIN [J].

COHEN, N ;

EICHEL, WF ;

LOPRESTI, RJ ;

NEUKOM, C ;

SAUCY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3505-3511

[5]

COREY EJ, 1968, TETRAHEDRON LETT, P5787

[6] STEREOSPECIFIC TOTAL SYNTHESIS OF DL-C18 CECROPIA JUVENILE HORMONE [J].

COREY, EJ ;

KATZENELLENBOGEN, JA ;

GILMAN, NW ;

ROMAN, SA ;

ERICKSON, BW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5618-+

[7] HOMOGENEOUS NUCLEOPHILE EXCHANGE .1. SIMPLE, HIGH-YIELD SYNTHESIS OF SOME HETERODIHALIDES [J].

HAHN, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1331-1333

[8]

HUISGEN R, 1970, TETRAHEDRON LETT, P3053

[9] SALT EFFECT ON REACTION OF ZINC CARBENOID [J].

KAWABATA, N ;

YAMASHIT.S ;

NODA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (08) :2580-+

[10] UMSETZUNG VON ALLYLHALOGENIDEN MIT DIAZOMETHAN UNTER KUPFERSALZ-KATALYSE [J].

KIRMSE, W ;

KAPPS, M ;

HAGER, RB .

CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (09) :2855-&

← 1 2 3 →