MONOCYCLIC TERPENE ALCOHOLS .8. P-MENTHA-2,4(8)-DIEN-9-OL AND P-MENTHA-2,4(8)-DIEN-10-OL

被引：5

作者：

CAMPS, F

机构：

[1] Departamento de Química Orgánica, Centro de Investigación y Desarrollo, Patronato “Juan de la Cierva” (C.S.I.C.), Zona Universitaria

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 06期

关键词：

D O I：

10.1021/jo01270a064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dehydration of ethyl 8-hydroxy-p-menth-3-en-9-oate (I) to afford dienic esters was studied under a variety of conditions. It was found that ethyl p-mentha-2,4(8)-dien-9-oate (V) was formed predominantly by phosphorus oxychloride-pyridine treatment of I, whereas pyrolysis of the acetate of I yielded ethyl p-mentha-2,4(8)- dien-10-oate (IV) and V in a 1:1 ratio. The same ratio was reached by thermal isomerization of V. p-Mentha- 2,4(8)-dien-9-ol and p-mentha-2,4(8)-dien-lO-ol were obtained by lithium aluminum hydride reduction of the corresponding esters. © 1968, American Chemical Society. All rights reserved.

引用

页码：2466 / &

共 16 条

[1] MONOCYCLIC TERPENE ALCOHOLS .2. P-MENTHAN-7-OLS P-MENTHAN-9-OLS AND P-MENTH-3-EN-9-OL [J].

ALBAIGES, J ;

CASTELLS, J ;

PASCUAL, J .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (11) :3507-&

[2]

BELLAMY LJ, 1958, INFRARED SPECTRA COM, P185

[3] PROTON MAGNETIC RESONANCE STUDIES OF CYCLIC COMPOUNDS .4. INFLUENCE OF ALKYL SUBSTITUENTS ON CHEMICAL SHIFTS OF RING PROTONS IN CYCLOHEXANE COMPOUNDS [J].

BOOTH, H .

TETRAHEDRON, 1966, 22 (02) :615-&

[4] MONOCYCLIC TERPENE ALCOHOLS .3. P-MENTH-4(8)-EN-9-OL AND TRANS- AND CIS-P-MENTH-8(10)-EN-9-OL [J].

CAMPS, F ;

CASTELLS, J ;

PASCUAL, J .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (11) :3510-&

[5]

CAMPS F, 1968, AN QUIM-INT, V64, P167

[6]

CASTELLS J, 1956, J CHEM SOC, P3245

[7] SOME TERPENIC CONSTITUENTS OF BURSERA GRAVEOLENS ( H. B. K. ) TR. ET PL. VAR. VILLOSULA CUATR [J].

CROWLEY, KJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (NOV) :4254-&

[8] STRUCTURE AND STEREOCHEMISTRY OF KETOACIDS DERIVED FROM MENTHOFURAN PHOTOPEROXIDE [J].

FOOTE, CS ;

WUESTHOF.MT ;

BURSTAIN, IG .

TETRAHEDRON, 1967, 23 (06) :2601-&

[9] PHOTOSENSITIZED OXYGENATION OF ALKYL-SUBSTITUTED FURANS [J].

FOOTE, CS ;

WUESTHOF.MT ;

WEXLER, S ;

BURSTAIN, IG ;

DENNY, R ;

SCHENCK, GO ;

SCHULTEE.KH .

TETRAHEDRON, 1967, 23 (06) :2583-&

[10] SYNTHESEN 3-SUBSTITUIERTER CYCLOHEXENON-DERIVATE [J].

GREWE, R ;

NOLTE, E ;

ROTZOLL, RH .

CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (03) :600-610

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