Reaction of silyl thioketones with lithium diethylphosphite : First observation of thia-brook rearrangement
Journal of organometallic chemistry Volume 611 Issue 1-2
Page 449-454
published_at 2000-10-06
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| File | |
| Title ( eng ) |
Reaction of silyl thioketones with lithium diethylphosphite : First observation of thia-brook rearrangement
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| Creator |
Sumi Koichi
Hagisawa Susumu
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| Source Title |
Journal of organometallic chemistry
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| Volume | 611 |
| Issue | 1-2 |
| Start Page | 449 |
| End Page | 454 |
| Abstract |
Reaction of silyl thioketone 7 with lithium diethylphosphite at –98 °C afforded an S-attack product 8 and a formal C-attack products 10 and 11, which were formed by S-to-C migration of the phosphoryl group in 8 followed by C-to-S migration of the silyl group (thia-Brook rearrangemnet), in a ratio depending on the conditions. The relative facility of the thia-Brook rearrangement was compared with that of the Brook rearrangement using the (t-butyldimethylsilyl) diphenylmethyl derivatives 22 and 23.
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| Keywords |
Inter-element linkage
Silyl thioketone
Thia-Brook rearrangement
Sulfur-phosphorus bond
sulfur-silicon bond
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| NDC |
Chemistry [ 430 ]
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| Language |
eng
|
| Resource Type | journal article |
| Publisher |
Elsevier Science
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| Date of Issued | 2000-10-06 |
| Rights |
Copyright (c) 2000 Elsevier Science S.A.
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| Publish Type | Author’s Original |
| Access Rights | open access |
| Source Identifier |
[ISSN] 0022-328X
[DOI] http://dx.doi.org/10.1016/S0022-328X(00)00482-4
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