The Synthesis Of C₄ And C₅ 13C-Labeled Benzo[A]Pyrene, Benzo[A]Pyrene-4, 5-Oxide And Derivatives. Studies Of The Reactions Of Benzo[A]Pyrene-4, 5-Oxide Using 13Cnmr

Author

Mark David Hylarides

Publication Date

3-16-1979

Abstract

Benzo[a]pyrene (BAP), BAP-4,5-oxide, and other derivatives which are 13c-labeled in the 4-and 5-positions were synthesized. The synthetic scheme involves an initial reaction of the lithioenolate of ethyl acetate-1-13c or ethyl acetate-2-13c with l,2-dihydrochrysen4(3H)-one. Subsequent dehydration and dehydrogenation gave ethyl 4-chryseneacetate-1-C (or 2-C). Partial reduction to the aldehyde 13 13 followed by cyclization gave BAP-5-C (and 4-C). Toe synchesis of 13 BAP-4,5-oxide-4-13c (and 5-c) involved saponification of ethyl 4-chryseneacetate-1-13c (and 2-13c), an intermediate in the synthesis of BAP, followed by cyclization of the resultant acid to BAP-5-ol13 s-c (and 4-13c). The crude phenol was oxidized to the o-quinone. Further reduction of the quinone to the trans-dihydrodiol followed by cyclization afforded the arene oxide.

Language

English

Document Type

Dissertation

Degree Name

Chemistry

Level of Degree

Doctoral

Department Name

Department of Chemistry and Chemical Biology

First Committee Member (Chair)

Guido Herman Daub

Second Committee Member

David Lee Vander Jagt

Third Committee Member

Illegible

Fourth Committee Member

Robert Edwin Tapscott

Comments

National Cancer Institute Grant no. CA-16871

Recommended Citation

Hylarides, Mark David. "The Synthesis Of C₄ And C₅ 13C-Labeled Benzo[A]Pyrene, Benzo[A]Pyrene-4, 5-Oxide And Derivatives. Studies Of The Reactions Of Benzo[A]Pyrene-4, 5-Oxide Using 13Cnmr." (1979). https://digitalrepository.unm.edu/chem_etds/257