Photochemistry of 6-trifluoromethyl-4,4-dimethyl-2-cyclohexenone

Cruciani, G.; Margaretha, P.

doi:10.1016/s0022-1139(00)83090-0

Search citation statements

Order By: Relevance

Paper Sections

Select...

Experimental Part1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1988

2006

Publication Types

Select...

Article3

Other2

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 9 publications

(1 citation statement)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Starting Materials. Cyclohexenones 4a [20], 4b [21], 4c [I I], 4d [22], 4e [23], 4f [22], 4g [20], and 4h [24] were synthesized according to literature.…”

Section: Experimental Partmentioning

confidence: 99%

Photorearrangement of 4,4‐Dimethylcyclohex‐2‐enones with Alkyl or Fluoro Substituents at C(5) and C(6): In Search of the Mechanism

Cruciani

Margaretha

1990

Helvetica Chimica Acta

View full text Add to dashboard Cite

The photorearrangement of cyclohex-2-enones 4 a 4 to bicyclo[3.1 .O]hexan-2-ones 5 and cyclopent-2-enones 6 ( A = 350 nm, MeCN) was investigated. Both the quantum yield (Q4 = 0.004 -0.024) and the product ratio (5/6 = 65: 35-31 : 69) vary only over a rather small range, indicating the rearrangement to be relatively insensitive to substituents on C(5) or C(6). Compounds 4b, 4c, and 4g with just one alkyl group at either C(6) or C(5) rearrange selectively to the diastereoisomer 5 with alkyl group and three-membered ring in trans-configuration, while 6-fluorocyclohex-2-enones 4d and 4f afford mixtures of diastereoisomeric bicyclohexanones. Mechanistic conclusions regarding an intermediate trimethylene biradical are presented.

show abstract

“…Starting Materials. Cyclohexenones 4a [20], 4b [21], 4c [I I], 4d [22], 4e [23], 4f [22], 4g [20], and 4h [24] were synthesized according to literature.…”

Section: Experimental Partmentioning

confidence: 99%