Photochemistry of 1,N-Diiodoalkanes
Why this work is in the frame
A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.
Bibliographic record
Abstract
This article reviews the photochemistry of 1,n-diiodoalkanes, with special emphasis on the involved intermediates. Photolysis of 1,1-diiodomethane produces homolytic cleavage of the C–I bond to give the α-iodo radical, which in solid matrix cannot dissociate but collapses to isodiiodomethane. However, in solution subsequent electron-transfer produces the α-iodo cation, which is able to achieve cyclo-propanation of olefins. In the case of 1,2-diiodides, their photolysis gives rise to β-iodoalkyl radicals which usually lose iodine very rapidly, forming a carbon-carbon double bond. Homolytic cleavage of 1,n-diiodoalkanes (n>2) affords n-iodo radicals which are stabilized by participation of the remaining iodine atom. The cyclic hypervalent iodine radicals thus generated have low reactivity towards oxygen and characteristic UV spectra whose λ max depends on the ring size. These intermediates can be photolyzed, with iodine extrusion and formation of 1,2-diphenylcycloalkanes. On the other hand, photoinduced electron-transfer between carbanionic nucleophiles and 1,n-diiodoalkanes produces n-iodo radicals, which couple with the nucleophile leading to radical anions. Intramolecular electron-transfer from the radical anion to the σ * MO of the remaining C–I bond may compete with intermolecular electron-transfer to the substrate. This type of processes have been used for the synthesis of mono- and disubstituted adamantane derivatives. Finally, photoinduced electron-transfer between aromatic amines and 1,n-diiodoperfluoroalkanes (n>2) allows the preparation of fluorine containing heteroaromatic compounds.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it