Stereoselectivity of Triplet Photocycloadditions:1 Diene-Carbonyl Reactions and Solvent Effects

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 3847-3854

  Griesbeck, Axel G ^a   Buhr, Stefan ^a   Fiege, Maren ^a   Schmickler, Hans ^a   Lex, Johann ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001308590     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971767l     Document Type: Article

References (87)

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84. One reviewer remarked that the endo/exo ratios (described, for example, in eq 3) do not vary in the same order as A values, which are often used to quantify the steric demand of a specific group. This is definitely true, and other contributions also have to be considered, e.g., spin dilution effects by the (conjugated or notconjugated) substituent. For cyclic monoalkenes, we have shown that steric effects are truly decisive (ref 7b-e), and A values are useful parameters to correlate with stereoselectivities. In our opinion, A values are, however, not applicable for description of steric interactions in biradicals such as F′. The cyano group (A value ca. 1.0) is expected to interact much stronger in the pseudoperpendicular conformation F′ than does a methyl group (A value 7.5).
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