Epic Quest Bio The case files
Case No. 124 · the exotic forty · have you seen this molecule?

Anti-Bredt olefin

the double bond the textbooks banned

File sealed

The detectives are still writing this one up. The poster and the facts are below; the film and the interrogation room open soon.

Booking photographs

Anti-Bredt olefin, front view, against a height chart in nanometers
FRONT
Anti-Bredt olefin, side view
SIDE · CID 13129031

The suspect, from its real atomic coordinates. Drag to turn it. Height chart in nanometers, ruled every 0.05 nm. This sheet of paper is over 100,000 times thicker. Mugshot: a computer model; nobody has a photo.

Rap sheet

Answers to
1-Norbornene (bicyclo[2.2.1]hept-1-ene).
Height
0.49 nm, standing on end.
Weight
0.16 zeptograms
Record
Broke Bredt’s rule (1924): no double bond at a bridgehead.
Build
A trans-alkene in a cage: twisted 35.5°, one end bent 20.1° toward a pyramid.
Strain
54.2 kcal/mol, yet still a double bond (bond order 1.86).
Habits
Grabs the nearest partner: furans, pyrroles, indene, anthracene.
First seen
Never, directly. First trapped in 1971; a 2017 textbook still says “too unstable to form.”
Last seen
In a sealed flask in a lab in Los Angeles, just before its capture.
0

of them ever directly observed. It is known only by what it leaves in traps.
You’ve never seen one. Neither has anyone else.

CASE FILE: McDermott, L. et al. (2024) A solution to the anti-Bredt olefin synthesis problem. Science 386, eadq3519.

The poster on the street

The wanted poster for Anti-Bredt olefin

This is the photocopied wanted poster for Anti-Bredt olefin, No. 124 of the exotic forty. They were made for noticeboards around Boston, Cambridge and the rest of the east coast.

Found one? Scan its QR code with your phone. If you're a signed-in player, the sighting goes on your record with +1 XP.

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