Photochemistry of Nitrogen-containing Thiocarbonyl Compounds

Sakamoto, Masami; Nishio, Takehiko

doi:10.3987/rev-02-sr1

Cited by 14 publications

(2 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cycloadditions, especially the photochemical [2 + 2] cycloaddition (thia-Paternò-Büchi reaction) of thiones and thioamides with olefins [15][16][17][18], and formal cycloadditions are alternative routes for the construction of thietane derivatives, especially multisubstituted thietanes. (Scheme 38).…”

Section: Synthesis Via Cycloadditionsmentioning

confidence: 99%

“…The intramolecular substitution of 3-mercaptoalkyl halides or sulfonates is a similar strategy for the preparation of thietanes [12][13][14]. Alternatively, inter-and intramolecular photochemical [2 + 2] cycloadditions (thia-Paternò-Büchi reactions) of alkenes and thiocarbonyl compounds are another important route for the synthesis of thietanes [15,16], especially, spirothietanes [17,18]. The formal [2 + 2] cycloadditions of hexafluorothioacetone and olefins are also applied in the preparation of bis(trifluoromethyl)-containing thietanes [19].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Thietanes are important aliphatic four-membered thiaheterocycles that are found in the pharmaceutical core and structural motifs of some biological compounds. They are also useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed, including inter- and intramolecular nucleophilic thioetherifications, photochemical [2 + 2] cycloadditions, ring expansions and contractions, nucleophilic cyclizations, and some miscellaneous methods. The recently developed methods provide some new strategies for the efficient preparation of thietanes and their derivatives. This review focuses on the synthetic methods to construct thietane backbones developed during 1966 to 2019.

show abstract

Section: Synthesis Via Cycloadditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Synthesis of Thietanes from Saturated Three‐membered Heterocycles

2020

Asian J Org Chem

View full text Add to dashboard Cite

Thietanes are important structural motifs of some biological compounds and useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed recently with readily available saturated three‐membered heterocycles as starting materials or key intermediates. Both saturated three membered heterocycle‐2‐methyl halides and sulfonates and thiiranes are widely utilized materials. Both nucleophilic and electrophilic ring expansions of thiiranes are efficient methods for synthesis of thietanes. In this Focus Review, we have described various strategies for the synthesis of strained four‐membered thiaheterocyclic thietanes from readily available strained and saturated three‐membered heterocycles.

show abstract