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Volumn 19, Issue 38, 1978, Pages 3513-3516

Allylsilanes in organic synthesis: A facile intramolecular allyl transfer, evidence for a non-concerted process

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EID: 0000863580 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)94979-2 Document Type: Article

Times cited : (69)

References (24)

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- Au-Yeung¹ Fleming²

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- This may reflect the hesitancy of practitioners of the synthesis of complex molecules to contemplate carrying a presumably labile allylsilane group through routine synthetic transformations needed to set the stage for the use of the allylsilane function. Based on the present studies (see also ref. 4) this chariness is largely unwarranted. A single intramolecular reaction of an allylsilane and an acetal has appeared:, Chem. Commun.
- (1976) J. Chem. Soc. , pp. 182
- Fleming¹ Pearce² Snowden³

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- (1967) J. Am. Chem. Soc. , vol.89 , pp. 2748
- Marshall¹ Andersen² Johnson³

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- (1970) J. Org. Chem. , vol.35 , pp. 858
- Marshall¹ Andersen² Schlicher³

13
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- Biogenetically patterned approaches to eudesmane sesquiterpenes. Total synthesis of (+-)-junenol
- (1972) Journal of the American Chemical Society , vol.94 , pp. 4361
- Schwartz¹ Crowell² Musser³

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- Chem. Commun.
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- Andersen¹ Uh² Smith³ Wuts⁴

16
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- 4 reduction. Silylation of the pure alcohols afforded comparison samples of ethers 4 and 6.

17
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- The instability of aldehyde 2 to gc at 140° is not due to ready thermal cyclization: none of the expected products (3→6) are obtained on collecting the eluted materials. Upon heating at 140–180° C in xylene, aldehyde 2 polymerizes without producing detectable quantities of cyclic products.The variables (mesh size, storage history, and precise degree of deactivation of the silica) that need to be controlled in order to direct the cyclization to alcohols or ethers are not fully determined.

18
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- 2 hydrolyses silyl ethers 4 and 6 independent of the quench employed.

19
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- 3Si-X:
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 3257
- Kuwajima¹ Nakamura²

21
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- The structures (and purity) of all numbered compounds in Scheme II are supported by the full complement of spectral data (NMR, IR, MS), including high resolution mass data (±5 mmass), and homogeneity by GC and HPLC or TLC.

22
- 84914374166
- Cyanide displacement at elevated temperatures leads to partial CSi bond cleavage. A related, but more facile, cleavage is observed with NaI in acetone at reflux.

23
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- (1977) J. Org. Chem. , vol.42 , pp. 3104
- Seyferth¹ Wursthorn² Mammarella³

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