The synthesis, structure, and some reactions of sterically hindred α-silylisoxazoles

Mark Borth; K. Dean Bowles; Ludwig Schlicksupp; N. R. Natale

doi:10.1016/S0022-328X(00)98908-3

The synthesis, structure, and some reactions of sterically hindred α-silylisoxazoles

Mark Borth, K. Dean Bowles, Ludwig Schlicksupp, N. R. Natale

University of Idaho

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

4-(4,5-Dihydro-4,4-dimethyl-2-isoxazolyl)-3-phenyl-5-silylmethylisozazole and 3-phenyl-5-silylmethyl-4-isoxazole-t-carboxamide derivatives were synthesized in synthetically useful yields from the corresponding oxazolyl-isoxazole or t-carboxamide by metalation of the isoxazole systems at the C(5) alkyl group followed by electrophilic quenching with either t-butylchlorodiphenylsilane or t-butylchlorodimethylsilane. The silylisoxazole systems were metalated at the C(5) position, producing the corresponding α-silyl carbanion, which upon quenching with MeOD produced C(5) deuterium incorporation. The reaction of silyloxazolylisoxazoles with titanium tetrachloride caused the oxazoline ring to open forming chloro-substituted carboxamide. The X-ray structure of a silyloxazolylisoxazole was obtained and indicates an "s-trans" ring juncture with respect to the heterocyclic rings.

Original language	English
Pages (from-to)	1-9
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	331
Issue number	1
DOIs	https://doi.org/10.1016/S0022-328X(00)98908-3
State	Published - Sep 1 1987

Funding

The authors thank the M.J. Murdock Charitable Trust of Research Corporation, the donors of the Petroleum Research Fund as administered by the American Chemical Society, the National Institutes of Health, BRSG SO7 RR07170 and the University of Idaho Research Council for generous financial support.

Funders	Funder number
BRSG SO7 RR07170
American Chemical Society

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10.1016/S0022-328X(00)98908-3

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@article{67cf6f50a8984a2c9242199783a5b228,

title = "The synthesis, structure, and some reactions of sterically hindred α-silylisoxazoles",

abstract = "4-(4,5-Dihydro-4,4-dimethyl-2-isoxazolyl)-3-phenyl-5-silylmethylisozazole and 3-phenyl-5-silylmethyl-4-isoxazole-t-carboxamide derivatives were synthesized in synthetically useful yields from the corresponding oxazolyl-isoxazole or t-carboxamide by metalation of the isoxazole systems at the C(5) alkyl group followed by electrophilic quenching with either t-butylchlorodiphenylsilane or t-butylchlorodimethylsilane. The silylisoxazole systems were metalated at the C(5) position, producing the corresponding α-silyl carbanion, which upon quenching with MeOD produced C(5) deuterium incorporation. The reaction of silyloxazolylisoxazoles with titanium tetrachloride caused the oxazoline ring to open forming chloro-substituted carboxamide. The X-ray structure of a silyloxazolylisoxazole was obtained and indicates an {"}s-trans{"} ring juncture with respect to the heterocyclic rings.",

author = "Mark Borth and Bowles, \{K. Dean\} and Ludwig Schlicksupp and Natale, \{N. R.\}",

note = "Funding Information: The authors thank the M.J. Murdock Charitable Trust of Research Corporation, the donors of the Petroleum Research Fund as administered by the American Chemical Society, the National Institutes of Health, BRSG SO7 RR07170 and the University of Idaho Research Council for generous financial support.",

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doi = "10.1016/S0022-328X(00)98908-3",

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T1 - The synthesis, structure, and some reactions of sterically hindred α-silylisoxazoles

AU - Borth, Mark

AU - Bowles, K. Dean

AU - Schlicksupp, Ludwig

AU - Natale, N. R.

N1 - Funding Information: The authors thank the M.J. Murdock Charitable Trust of Research Corporation, the donors of the Petroleum Research Fund as administered by the American Chemical Society, the National Institutes of Health, BRSG SO7 RR07170 and the University of Idaho Research Council for generous financial support.

PY - 1987/9/1

Y1 - 1987/9/1

N2 - 4-(4,5-Dihydro-4,4-dimethyl-2-isoxazolyl)-3-phenyl-5-silylmethylisozazole and 3-phenyl-5-silylmethyl-4-isoxazole-t-carboxamide derivatives were synthesized in synthetically useful yields from the corresponding oxazolyl-isoxazole or t-carboxamide by metalation of the isoxazole systems at the C(5) alkyl group followed by electrophilic quenching with either t-butylchlorodiphenylsilane or t-butylchlorodimethylsilane. The silylisoxazole systems were metalated at the C(5) position, producing the corresponding α-silyl carbanion, which upon quenching with MeOD produced C(5) deuterium incorporation. The reaction of silyloxazolylisoxazoles with titanium tetrachloride caused the oxazoline ring to open forming chloro-substituted carboxamide. The X-ray structure of a silyloxazolylisoxazole was obtained and indicates an "s-trans" ring juncture with respect to the heterocyclic rings.

AB - 4-(4,5-Dihydro-4,4-dimethyl-2-isoxazolyl)-3-phenyl-5-silylmethylisozazole and 3-phenyl-5-silylmethyl-4-isoxazole-t-carboxamide derivatives were synthesized in synthetically useful yields from the corresponding oxazolyl-isoxazole or t-carboxamide by metalation of the isoxazole systems at the C(5) alkyl group followed by electrophilic quenching with either t-butylchlorodiphenylsilane or t-butylchlorodimethylsilane. The silylisoxazole systems were metalated at the C(5) position, producing the corresponding α-silyl carbanion, which upon quenching with MeOD produced C(5) deuterium incorporation. The reaction of silyloxazolylisoxazoles with titanium tetrachloride caused the oxazoline ring to open forming chloro-substituted carboxamide. The X-ray structure of a silyloxazolylisoxazole was obtained and indicates an "s-trans" ring juncture with respect to the heterocyclic rings.

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DO - 10.1016/S0022-328X(00)98908-3

M3 - Article

AN - SCOPUS:0040485934

SN - 0022-328X

VL - 331

SP - 1

EP - 9

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1

ER -

The synthesis, structure, and some reactions of sterically hindred α-silylisoxazoles

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