Unusual rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2,5- disubstituted oxazoles

Adrian D Clark; Wit K Janowski; Rolf H Prager

doi:10.1016/S0040-4020(98)01171-5

Unusual rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2,5- disubstituted oxazoles

Adrian D Clark
, Wit K Janowski
, Rolf H Prager

College of Science and Engineering

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

17 Citations (Scopus)

Abstract

Flash vacuum pyrolysis of 2-aroyl-3-phenylisoxazol-5(2H)-ones leads to good yields of 2-aryl-4-phenyloxazoles, and smaller quantities of 2-aryl-5- phenyloxazoles and 5-aryl-2-phenyloxazoles. The mechanism of formation of the 2,5-disubstituted products has been investigated by ¹³C and substituent labelling, and a non-statistical breakdown of a symmetrical intermediate is invoked to rationalise the product formation.

Original language	English
Pages (from-to)	3637-3648
Number of pages	12
Journal	Tetrahedron
Volume	55
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4020(98)01171-5
Publication status	Published - 19 Mar 1999

Access to Document

10.1016/S0040-4020(98)01171-5Licence: In Copyright

Cite this

@article{4083f4d49b8e4f0fb7a4eb2c5798505f,

title = "Unusual rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2,5- disubstituted oxazoles",

abstract = "Flash vacuum pyrolysis of 2-aroyl-3-phenylisoxazol-5(2H)-ones leads to good yields of 2-aryl-4-phenyloxazoles, and smaller quantities of 2-aryl-5- phenyloxazoles and 5-aryl-2-phenyloxazoles. The mechanism of formation of the 2,5-disubstituted products has been investigated by 13C and substituent labelling, and a non-statistical breakdown of a symmetrical intermediate is invoked to rationalise the product formation.",

author = "Clark, \{Adrian D\} and Janowski, \{Wit K\} and Prager, \{Rolf H\}",

year = "1999",

month = mar,

day = "19",

doi = "10.1016/S0040-4020(98)01171-5",

language = "English",

volume = "55",

pages = "3637--3648",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "12",

}

TY - JOUR

T1 - Unusual rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2,5- disubstituted oxazoles

AU - Clark, Adrian D

AU - Janowski, Wit K

AU - Prager, Rolf H

PY - 1999/3/19

Y1 - 1999/3/19

N2 - Flash vacuum pyrolysis of 2-aroyl-3-phenylisoxazol-5(2H)-ones leads to good yields of 2-aryl-4-phenyloxazoles, and smaller quantities of 2-aryl-5- phenyloxazoles and 5-aryl-2-phenyloxazoles. The mechanism of formation of the 2,5-disubstituted products has been investigated by 13C and substituent labelling, and a non-statistical breakdown of a symmetrical intermediate is invoked to rationalise the product formation.

AB - Flash vacuum pyrolysis of 2-aroyl-3-phenylisoxazol-5(2H)-ones leads to good yields of 2-aryl-4-phenyloxazoles, and smaller quantities of 2-aryl-5- phenyloxazoles and 5-aryl-2-phenyloxazoles. The mechanism of formation of the 2,5-disubstituted products has been investigated by 13C and substituent labelling, and a non-statistical breakdown of a symmetrical intermediate is invoked to rationalise the product formation.

UR - https://www.scopus.com/pages/publications/0033582977

U2 - 10.1016/S0040-4020(98)01171-5

DO - 10.1016/S0040-4020(98)01171-5

M3 - Article

AN - SCOPUS:0033582977

SN - 0040-4020

VL - 55

SP - 3637

EP - 3648

JO - Tetrahedron

JF - Tetrahedron

IS - 12

ER -

Unusual rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2,5- disubstituted oxazoles

Abstract

Access to Document

Other files and links

Fingerprint

Cite this