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Volumn 61, Issue 20, 1996, Pages 7045-7055

Antenna-initiated photochemistry in polyfunctional steroids. Intramolecular singlet and triplet energy transfer between aryl, ketone, and alkene groups in 6β-(Dimethylphenylsiloxy)-5β-androstanes 1

Author keywords

[No Author keywords available]

Indexed keywords

ANDROSTANE DERIVATIVE;

EID: 0029826471     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952202x     Document Type: Article
Times cited : (15)

References (32)
  • 1
    • 0346923609 scopus 로고    scopus 로고
    • Organic Photochemistry. 112. Part 111: Post, A. J.; Morrison, H. J. Org. Chem. 1996, 61, 1560-1561. Presented, in part, at the 209th National Meeting of the American Chemical Society, 1995, Anaheim, CA. Abstracted from the Doctoral Dissertation of S. A. Jiang, Purdue University, Aug 1995.
    • (1996) J. Org. Chem. , vol.61 , pp. 1560-1561
    • Post, A.J.1    Morrison, H.2
  • 14
    • 3643105492 scopus 로고    scopus 로고
    • note
    • Interestingly, a second, downfield H-4 resonance is also coupled with the vinyl methyl resonance.
  • 18
    • 3643143017 scopus 로고    scopus 로고
    • note
    • Analogous results were obtained by irradiation of the analogous monoketone, 6β-(dimethylphenylsiloxy)-5β-cholestan-3-one (7), in cyclohexane with 266 nm and 308 nm laser light. The β (24) and a (25) alcohols were isolated in a ratio of 1:4.5. Details may be found in ref 15.
  • 19
    • 3643067992 scopus 로고
    • Doctoral Dissertation, Purdue University, W. Lafayette, IN, Aug
    • Jiang, S. A. Doctoral Dissertation, Purdue University, W. Lafayette, IN, Aug 1995.
    • (1995)
    • Jiang, S.A.1
  • 20
    • 0004344770 scopus 로고
    • University Science Books: Mill Valley, CA
    • Turro, N. J. Modern Molecular Photochemistry; University Science Books: Mill Valley, CA, 1991; pp 252, 436.
    • (1991) Modern Molecular Photochemistry , pp. 252
    • Turro, N.J.1
  • 21
    • 3643103401 scopus 로고    scopus 로고
    • note
    • In fact, some reaction enhancement was observed in the presence of piperylene. This is due to the low conversion conditions under which the quenching studies were run. We have observed that secondary photochemistry destroys the photoproducts.
  • 27
    • 3042988525 scopus 로고
    • Distance data were obtained by calculations using a Silicon Graphics Personal Iris 4D/35 Computer with MacroModel V3.5X Software: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. MM2* method: Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 8127
    • Allinger, N.L.1
  • 28
    • 3643077398 scopus 로고    scopus 로고
    • note
    • We find it striking that direct excitation of the C17 carbonyl group with 308 nm light in 33 and 34 also leads to isomerization of the C3 alkene (4.6 and 10% of the product for 33 and 34, respectively; Table 6). Though these results imply intra-TTET from the C17 ketone triplet to C3, such an explanation would be inconsistent with the lack of ISC we have observed in a C17 ketone. Studies of substrates lacking the C6 DPSO group are in progress.
  • 29
    • 33845379281 scopus 로고
    • Kurth, M. J.; O'Brien, M. J.; Hope, H.; Yanuck, M. J. Org. Chem. 1985, 50, 2626-2632. Parish, E. J.; Luo, C.; Parish, S.; Heidepriem, R. W. Synth. Commun. 1992, 22(19), 2839-2847.
    • (1985) J. Org. Chem. , vol.50 , pp. 2626-2632
    • Kurth, M.J.1    O'Brien, M.J.2    Hope, H.3    Yanuck, M.4
  • 30


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.