Acid-catalyzed rearrangement of aromatic ethers. Model studies and application to imaging

H. Stover; S. Matuszczak; R. Chin; K. Shimizu; C. G. Willson; J. M.J. Frechet

Acid-catalyzed rearrangement of aromatic ethers. Model studies and application to imaging

H. Stover^*, S. Matuszczak, R. Chin, K. Shimizu, C. G. Willson, J. M.J. Frechet

^*Corresponding author for this work

Research output: Contribution to journal › Conference article › peer-review

6 Scopus citations

Abstract

A variety of polymers incorporating appropriate benzylic or allylic ether functionalities in their main-chain were shown to be excellent dry-developing imaging systems. In view of the excellent results which are obtained in the photocrosslinking of the copolymers, some of the mechanistic details of the crosslinking process were explored. In particular, much information can be obtained from model studies with low molecular weight compounds instead of the copolymer. The models chosen for this study were benzyl acetate, or 4-isopropyl-benzyl acetate, and 4-isopropyl phenol. The model reactions were carried out within the confines of a NMR tube in deuterochloroform using 10 mole % triflic acid to trigger the reaction instead of the photogenerated superacid.

Original language	English (US)
Pages (from-to)	412-416
Number of pages	5
Journal	Polymeric Materials Science and Engineering, Proceedings of the ACS Division of Polymeric Materials Science and Engineering
Volume	61
State	Published - 1989
Externally published	Yes
Event	Proceedings of the ACS Division of Polymeric Materials: Science and Engineering - Miami Beach, FL, USA Duration: Sep 11 1989 → Sep 18 1989

ASJC Scopus subject areas

Chemical Engineering (miscellaneous)
Polymers and Plastics

Cite this

@article{894fd3622b9443d5951c265ee6fe4e89,

title = "Acid-catalyzed rearrangement of aromatic ethers. Model studies and application to imaging",

abstract = "A variety of polymers incorporating appropriate benzylic or allylic ether functionalities in their main-chain were shown to be excellent dry-developing imaging systems. In view of the excellent results which are obtained in the photocrosslinking of the copolymers, some of the mechanistic details of the crosslinking process were explored. In particular, much information can be obtained from model studies with low molecular weight compounds instead of the copolymer. The models chosen for this study were benzyl acetate, or 4-isopropyl-benzyl acetate, and 4-isopropyl phenol. The model reactions were carried out within the confines of a NMR tube in deuterochloroform using 10 mole % triflic acid to trigger the reaction instead of the photogenerated superacid.",

author = "H. Stover and S. Matuszczak and R. Chin and K. Shimizu and Willson, {C. G.} and Frechet, {J. M.J.}",

year = "1989",

language = "English (US)",

volume = "61",

pages = "412--416",

journal = "Polymeric Materials Science and Engineering, Proceedings of the ACS Division of Polymeric Materials Science and Engineering",

issn = "0743-0515",

note = "Proceedings of the ACS Division of Polymeric Materials: Science and Engineering ; Conference date: 11-09-1989 Through 18-09-1989",

}

Acid-catalyzed rearrangement of aromatic ethers. Model studies and application to imaging. / Stover, H.; Matuszczak, S.; Chin, R. et al.
In: Polymeric Materials Science and Engineering, Proceedings of the ACS Division of Polymeric Materials Science and Engineering, Vol. 61, 1989, p. 412-416.

Research output: Contribution to journal › Conference article › peer-review

TY - JOUR

T1 - Acid-catalyzed rearrangement of aromatic ethers. Model studies and application to imaging

AU - Stover, H.

AU - Matuszczak, S.

AU - Chin, R.

AU - Shimizu, K.

AU - Willson, C. G.

AU - Frechet, J. M.J.

PY - 1989

Y1 - 1989

N2 - A variety of polymers incorporating appropriate benzylic or allylic ether functionalities in their main-chain were shown to be excellent dry-developing imaging systems. In view of the excellent results which are obtained in the photocrosslinking of the copolymers, some of the mechanistic details of the crosslinking process were explored. In particular, much information can be obtained from model studies with low molecular weight compounds instead of the copolymer. The models chosen for this study were benzyl acetate, or 4-isopropyl-benzyl acetate, and 4-isopropyl phenol. The model reactions were carried out within the confines of a NMR tube in deuterochloroform using 10 mole % triflic acid to trigger the reaction instead of the photogenerated superacid.

AB - A variety of polymers incorporating appropriate benzylic or allylic ether functionalities in their main-chain were shown to be excellent dry-developing imaging systems. In view of the excellent results which are obtained in the photocrosslinking of the copolymers, some of the mechanistic details of the crosslinking process were explored. In particular, much information can be obtained from model studies with low molecular weight compounds instead of the copolymer. The models chosen for this study were benzyl acetate, or 4-isopropyl-benzyl acetate, and 4-isopropyl phenol. The model reactions were carried out within the confines of a NMR tube in deuterochloroform using 10 mole % triflic acid to trigger the reaction instead of the photogenerated superacid.

UR - http://www.scopus.com/inward/record.url?scp=0024882550&partnerID=8YFLogxK

M3 - Conference article

AN - SCOPUS:0024882550

SN - 0743-0515

VL - 61

SP - 412

EP - 416

JO - Polymeric Materials Science and Engineering, Proceedings of the ACS Division of Polymeric Materials Science and Engineering

JF - Polymeric Materials Science and Engineering, Proceedings of the ACS Division of Polymeric Materials Science and Engineering

T2 - Proceedings of the ACS Division of Polymeric Materials: Science and Engineering

Y2 - 11 September 1989 through 18 September 1989

ER -

Acid-catalyzed rearrangement of aromatic ethers. Model studies and application to imaging

Abstract

ASJC Scopus subject areas

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