Reactions of 1,1-bis(silylmethyl)-1-alkene with N-halosuccinimide and ozone

被引：1

作者：

Uenishi, J ^{[1
]}

Tanaka, Y ^{[1
]}

Ohmi, M ^{[1
]}

Shimomura, H ^{[1
]}

Kawai, N ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Yamashina, Kyoto 6078412, Japan

来源：

HETEROCYCLES | 2005年 / 66卷

关键词：

allylsilane; protodesilylation; halodesilylation; oxidative desilylation; ozone;

D O I：

10.3987/COM-05-S(K)37

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic reactions of 3-phenyl-1,1-bis(trimethylsilymethyl)-1-propene (1) and 1,1-bis[dimethyl(phenyl)silylmethyl]-3-phenyl-1-propene (4) are described. Protodesilylation of 1 with PPTS gave 2-substituted allylsilane (2) in excellent yield. Halogenation of 4 with N-halosuccimide gave a mixture of 3-halo-5-phenyl-2-silylmethyl-l-pentene (5) and 3-halo-5-phenyl-1,2bis(silylmethyl)-1-pentene (6). The reaction of 1 and 4 with ozone gave no carbonyl compounds but gave 3-hydoxy-5-phenyl-2-silylmethyl-1-pentene (7).

引用

页码：595 / 602

页数：8

共 16 条

[1] Peroxycarbenium-mediated C-C bond formation: Applications to the synthesis of hydroperoxides and peroxides
Dussault, PH
Lee, IQ
Lee, HJ
Lee, RJ
Niu, QJ
Schultz, JA
Zope, UR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) : 8407 - 8414
[2] Reaction of allylsilanes and allylstannanes with alkynes catalyzed by electrophilic late transition metal chlorides
Fernández-Rivas, C
Méndez, M
Nieto-Oberhuber, C
Echavarren, AM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) : 5197 - 5201
[3] Stereochemical control in organic synthesis using silicon-containing compounds
Fleming, I
Barbero, A
Walter, D
[J]. CHEMICAL REVIEWS, 1997, 97 (06) : 2063 - 2192
[4] New trimethylenemethane dianion synthons:: Application to the preparation of substituted perhydrofuro[2,3-b]furans
Lorenzo, E
Alonso, F
Yus, M
[J]. TETRAHEDRON, 2000, 56 (12) : 1745 - 1757
[5] Stereoselective approach to C-glycosylasparagines
Lygo, B
Andrews, BI
Slack, D
[J]. TETRAHEDRON LETTERS, 2003, 44 (50) : 9039 - 9041
[6] OCHIAI M, 1982, TETRAHEDRON LETT, V23, P5419
[7] Reactions of allylsilanes with iminium salts: Ene reactions with inverse electron demand
Ofial, AR
Mayr, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) : 5823 - 5830
[8] 4+3 and fluorinative 4+3 cycloadditions of alkyne 1,4-diether dicobalt complexes
Patel, MM
Green, JR
[J]. CHEMICAL COMMUNICATIONS, 1999, (06) : 509 - 510
[9] Orally active, antimalarial, anticancer, artemisinin-derived trioxane dimers with high stability and efficacy
Posner, GH
Paik, IH
Sur, S
McRiner, AJ
Borstnik, K
Xie, SJ
Shapiro, TA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (06) : 1060 - 1065
[10] Convergent synthesis of a polyol chain with 4-acetoxy-1,3-dioxanes using a 1,1-bis((trimethylsilyl)methyl) ethene linchpin
Rychnovsky, SD
Fryszman, O
Khire, UR
[J]. TETRAHEDRON LETTERS, 1999, 40 (01) : 41 - 44

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