Polar [4+2]‐ and [4+4]‐Photocycloadditions: Effects of Hybridization in Diradicals | Zendy

Kaupp Gerd | Zendy; Grüter HeinzWilli | Zendy

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Polar [4+2]‐ and [4+4]‐Photocycloadditions: Effects of Hybridization in Diradicals

Author(s) -

Kaupp Gerd,

Grüter HeinzWilli

Publication year - 1979

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.197908811

Subject(s) - anthracene , polar , substituent , adduct , chemistry , polar effect , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , physics , astronomy

The control of photochemical reactions by polar substituents is of value for preparative applications. For example, anthracene (1a) reacts with butadiene to give the [4+2]‐ (2a) and the [4+4] adduct (3a) in the ratio of 20:1. The carbonitrile (1b) , on the other hand, leads to (2b), (3b) , and (4) (secondary product of a (3b) ‐isomer) in the ratio of 1:3.2:13.3. The polar substituent thus suppresses the [4 + 2] reaction ( a: X H; b: X CN).

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