REACTION OF ALPHA OLEFINS WITH PARAFORMALDEHYDE AND HYDROGEN HALIDES . A NOVEL TETRAHYDROPYRAN SYNTHESIS

被引：55

作者：

STAPP, PR

机构：

[1] Research Division, Phillips Petroleum Company, Bartlesville, Oklahoma

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 03期

关键词：

D O I：

10.1021/jo01255a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new reaction has been discovered in which a olefins are condensed with paraformaldehyde and hydrogen halides to give 3-alkyl-4-halotetrahydropyrans. The best yields using hydrogen chloride as the halide component were obtained at -60 to -70°. Isolation of an intermediate homoallylic alcohol provides substantiation of a proposed mechanism. © 1969, American Chemical Society. All rights reserved.

引用

收藏

页码：479 / &

相关论文

共 27 条

[1]

AGAMI C, 1966, CR ACAD SCI C CHIM, V263, P153

[2] THE OLEFIN ALDEHYDE CONDENSATION - THE PRINS REACTION [J].

ARUNDALE, E ;

MIKESKA, LA .

CHEMICAL REVIEWS, 1952, 51 (03) :505-555

[3] alpha-methylenic reactivity in Olefinic systems Part I The prins reaction with propylene [J].

Baker, JW .

JOURNAL OF THE CHEMICAL SOCIETY, 1944, :296-301

[4] THE MINERAL ACID-CATALYZED REACTION OF CYCLOHEXENE WITH FORMALDEHYDE [J].

BLOMQUIST, AT ;

WOLINSKY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (22) :6025-6030

[5]

BROOKS BT, 1955, CHEMISTRY PETROLEUM, V3, P455

[6]

COLONGE J, 1955, CR HEBD ACAD SCI, V240, P1552

[7]

COLONGE J, 1956, B SOC CHIM FR, V23, P824

[8]

Cope A.C., 2011, ORG REACTIONS, V9, P107

[9] STEREOCHEMICAL STUDIES OF OLEFINIC COMPOUNDS .5. FURTHER OBSERVATIONS ON THE RING FISSION OF 3-CHLOROTETRAHYDRO-FURANS AND 3-CHLOROTETRAHYDRO-PYRANS [J].

CROMBIE, L ;

GOLD, J ;

HARPER, SH ;

STOKES, BJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JAN) :136-142

[10] STEREOCHEMICAL STUDIES OF OLEFINIC COMPOUNDS .2. RING SCISSION OF 2-1'-HALOGENOALKYLTETRAHYDROFURANS AND 3-HALOGENO-2-ALKYLTETRAHYDROPYRANS AS A ROUTE TO ALK-4-EN-1-OLS OF KNOWN CONFIGURATION AND AS A METHOD OF CHAIN EXTENSION BY 5 METHYLENE GROUPS [J].

CROMBIE, L ;

HARPER, SH .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, :1707-1714