Photochemistry of Enolic Systems. II. Irradiation of Dienol Acetates

Malka Gorodetsky, Yehuda Mazur

Research output: Contribution to journalArticlepeer-review

18 Scopus citations


Irradiation of dienol acetates derived from testosterone and 4-methyltestosterone with a low pressure mercury lamp is described. The irradiation involves acetyl rearrangement from oxygen at C-3 to the carbon at C-4 and C-6. Thus androsta-3,5-diene-3,17β-diol diacetate (1) resulted in 2 and 8; 4α-methylandrosta-3,5-diene-3,17β-diol diacetate (13) yielded the corresponding 4-methyl homologs 14 and 15. The chemistry and stereochemistry of the isolated products support the previously postulated cage mechanism and stereoelectronic control for this photochemical reaction. 1b The stability relations of the 6-acetyltestosterone epimers are discussed and compared with those of the corresponding epimeric saturated derivatives. The unusual stability of the 6β-acetyl-testosterone is explained by electronic factors.

Original languageEnglish
Pages (from-to)5213-5218
Number of pages6
JournalJournal of the American Chemical Society
Issue number23
StatePublished - 1 Dec 1964
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


Dive into the research topics of 'Photochemistry of Enolic Systems. II. Irradiation of Dienol Acetates'. Together they form a unique fingerprint.

Cite this