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

页码：479 / &

共 27 条

[1] AGAMI C, 1966, CR ACAD SCI C CHIM, V263, P153
[2] THE OLEFIN ALDEHYDE CONDENSATION - THE PRINS REACTION
ARUNDALE, E
MIKESKA, LA
[J]. CHEMICAL REVIEWS, 1952, 51 (03) : 505 - 555
[3] alpha-methylenic reactivity in Olefinic systems Part I The prins reaction with propylene
Baker, JW
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1944, : 296 - 301
[4] THE MINERAL ACID-CATALYZED REACTION OF CYCLOHEXENE WITH FORMALDEHYDE
BLOMQUIST, AT
WOLINSKY, J
[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
CROMBIE, L
GOLD, J
HARPER, SH
STOKES, BJ
[J]. 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
CROMBIE, L
HARPER, SH
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, : 1707 - 1714

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