QUINONES AND QUINONE METHIDES .5. FURTHER REARRANGEMENTS OF THE DIMER FROM 5-METHOXY-2-(4-METHOXYPHENYLMETHYL)-1,4-BENZOQUINONE

被引：7

作者：

JURD, L

ROITMAN, JN

机构：

[1] Western Regional Research Laboratory, Science and Education Administration, U.S. Department of Agriculture, Berkeley

来源：

TETRAHEDRON | 1979年 / 35卷 / 13期

关键词：

D O I：

10.1016/0040-4020(79)80017-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In strongly acid solutions the dimer 3 dissociates to the quinone 1 and quinone methide 2 which recombine with elimination of p-methoxybenzyl alcohol to form the xanthylium salt 9a. With zinc and acetic acid 3 yields isormeric meso- and dl-ethylenediquinol derivatives 14a. Sodium borohydride reduction of 3 yields an alcoholic quinol 5a which rapidly reoxidizes to the spiro-tetrahydrofuran derivative 24a. Possible mechanisms which may be involved in the formation of these rearranged products are discussed. © 1979.

引用

页码：1567 / 1574

页数：8

共 43 条

[1] QUINONES AND QUINONE METHIDES .4. DIMERIZATION REACTIONS OF 2-PHENYLMETHYL-5-METHOXY-1,4-BENZOQUINONES
JURD, L
ROITMAN, JN
WONG, RY
TETRAHEDRON, 1979, 35 (09) : 1041 - 1054
[2] QUINONES AND QUINONE METHIDES .2. CYCLIZATION AND HYDRATION REACTIONS OF 2-CINNAMYL-5-METHOXY-1,4-BENZOQUINONES
JURD, L
ROITMAN, JN
TETRAHEDRON, 1978, 34 (01) : 57 - 62
[3] QUINONES AND QUINONE METHIDES .8. OXIDATION-PRODUCTS OF THE SCREWWORM CHEMOSTERILANT, 2,4-BIS(1,1-DIMETHYLETHYL)-6-(4-METHOXYPHENYLMETHYL)PHENOL
JURD, L
WONG, RY
AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (08) : 1633 - 1644
[4] 2-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone (isoflavonequinone)
Aree, T
Tip-pyang, S
Seesukphronrarak, S
Chaichit, N
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O363 - O365
[5] 6-METHOXY-3-METHYLBENZOFURANO-4,7-QUINONE - DIMERS OF 3-METHYL-BENZOFURANS - AND TAUTOMERISM IN 2-ACETYL-3-HYDROXY-5-METHOXY-1,4-BENZOQUINONE
CAVELL, BD
MACMILLA.J
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (04): : 310 - &
[6] 1,4-CARBAZOLQUINONES FROM PARA-BENZOQUINONE AND PRIMARY ALIPHATIC-AMINES - ALLEGED AND THE REAL 2-METHYLAMINO-BENZOQUINONE - STUDIES ON QUINONES .5.
OTT, R
PINTER, E
KAJTNA, P
MONATSHEFTE FUR CHEMIE, 1979, 110 (01): : 51 - 62
[7] Liquid phase oxidation of 4-methylanisole to 2-methoxy-5-methyl-1,4-benzoquinone over Cu/MCM-41
Li, Bin
Wang, Jiliang
Li, Junjie
Xu, Yonghua
Fu, Jipin
Yao, Wenhua
Zi, Guoli
Wang, Wei
Wang, Jiaqiang
CATALYSIS COMMUNICATIONS, 2009, 10 (12) : 1599 - 1603
[8] THIELE-WINTER ACETOXYLATION OF QUINONES .5. STRUCTURES OF MAJOR TRIACETATE PRODUCT FROM "5-METHYL-3-T-BUTYL-1,2-BENZOQUINONE AND OF BY-PRODUCT FROM "2-METHYL-6-T-BUTYL-1,4-BENZOQUINONE
MCOMIE, JFW
SALEH, SA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (03): : 384 - 388
[9] Stabilization of ortho-quinone methides by a bis(sulfonium ylide) derived from 2,5-dihydroxy-[1,4]benzoquinone
Patel, Anjan
Netscher, Thomas
Rosenau, Thomas
TETRAHEDRON LETTERS, 2008, 49 (15) : 2442 - 2445
[10] TOXICANTS FROM MANGROVE PLANTS .5. ISOLATION OF THE PISCICIDE, 2-HYDROXY-5-METHOXY-3-UNDECYL-1,4 BENZOQUINONE (5-O-METHYLEMBELIN) FROM AEGICERAS-CORNICULATUM
GOMEZ, E
DELACRUZGIRON, O
DELACRUZ, AA
JOSHI, BS
CHITTAWONG, V
MILES, DH
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (03): : 649 - 651

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