Conformational control of photochemical behavior. Cyclohexyl phenyl ketone

✍ Scribed by Frederick D. Lewis; Richard W. Johnson

• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 240 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96204-5

✦ Synopsis

Ground state molecular conformations can influence photochemical behavior m cases where excited state reactions are more rapti than conformational momerlzatlon. 2 Our mterest m the role of molecular conformation 111 photochemistry led us to reexamine the photochemistry of cyclohexyl phenyl ketone @) and its CIS-and -4-i-butyl derivatives (2 and 2). Previous mvestlgatlons of J and 2 have revealed mefflclent formation of acetophenone, s presumably via consecutive type II elrminatlons (eq 1,2). The antmlpated prnnary photoproducts 4 and/or 2 4 have not been ldentlfred. The relative stablllty of _j and 2 has been attributed to the maccesslbllrty of the v-hydrogen to the carbonyl group m the more stable conformers of _j (equatorial) and 2 (dlequatorml twist boat).)b The mefflclency of product formation from 1 seemed surprising for the followmg reasons. (a) at least several percent of the ground state molecules